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Stereochemistry abstracts
STEREOCHEMISTRY ABSTRACTS
Tetrahedron: Asymmetry 1997, 8, 497
J. T. Dougherty, J. R. Flisak. J. Hayes, I. Lantos, L. Liu* and L. Tucker
E.e. = 99% (by chiral HPLC using a CHIRALCEL-OD column) [O~]D 25 =
NO2
+19.9 (c = 1.0, DMF)
(S)-O-(2-nitrobenzyl)-N-(6-benzyloxy-2.3dihydrobenzofuran- 3-yl)-hydroxylamine
C22H~20~ Source of chirality: asymm, reduction Absolute configuration: 3S (assigned by correlation)
Nicolas Gautier, Nicolas Noiret*, Caroline Nugier-Chauvin and Henri Patin.
I
Tetrahedron:Asymmetry 1997, 8, 501
E.e.= 92% (;H-NMR)
ee
[O~]D20-- -3.71 (C 0.62, EtOH) Cell;sOS 1-butyl-3-butenyl sulphoxide
Source of chirality: the DAG methodology Absolute configuration: R
Tetrahedron: Asymmetry 1997,
R. C. Griesbach. D. P. G. Hamon and R. J. Kennedy,
8, 507
E.e.=98% [by NMR Eu(hfc) 3 shift experiments on the derived monoacetates]
OH
OH
Source of chirality: asymm, synth. (asymmetric dihydroxylation) Absolute configuration 2S confirmed by conversion to (S)-2(6-methoxy-2-naphthyl) propanoic acid
C14H1603 2-(6-methoxy-2-naphthyl)propan- 1,2-diol
I Tetrahedron:Asymmetry 1997,
R. C. Griesbach, D. P. G. Hamon and R. J. Kennedy,
8, 507
E.e.=98% [by NMR Eu(hfc)3 shift experiments on the derived monoacetates]
F
Source of chirality: asymm, synth. (asymmetric dihydroxylation)
OH
OH
Absolute configuration 2S confirmed by conversion to (S)-2(3-fluoro-4-phenylphenyl) propanoic acid
CI5H15FO2 2-( 3-fluoto-4-phenylphenyl)propan- 1,2-diol
A93
Tetrahedron:Asymmetry1997,8, 511
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal E.e. > 98°/.
O
~O ~
[Ot]D= -43.2 (c 1.0, CHCI3) Source of chirality:D(+)-Ribonic7-1actone
CO2Et
Absolute configuration:l R, 2R, 3R, 5S, 6S
C15H2oO5 (-)-(1 R, 2R, 3R, 5S, 6S)-Ethyl-2,3-cyclohexylidenedioxy-4-oxobicyclo[3,1,0]hexane-6-carboxylate
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
Tetrahedron:Asymmetry1997,8, 511
HN--CO
~ O
I OC/,,..NH
E.e. > 98% [(X]D= -107.2 (C 1.0, CHCI3)
~ C O 2 E t
Source of chirality:D(+)-Ribonic7-1actone Absolute configuration:l S, 2S, 3S, 4R, 5R, 6R
C17H22N203 (-)-(1 S, 2S, 3S, 4R, 5R, 6R)-Ethyl-3,4-cyclohexylidenedioxybicyclo[3,1,0]hexane-2-spiro-5'-hYdantoine-6carboxylate
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
~
I Tetrahedron:Asymmetry1997,8, 511
NCt,~NHCOCH3
E.e. > 98% [(X]D= -105.7 (cl.0, CHCI3)
o~~CO2
Source of chirality:D(+)-Ribonic7-1actone
Et
Absolute configuration: 1S, 2S, 3S, 4R, 5R, 6R
C1sH24N205 (-)-(1S, 2S, 3S, 4R, 5R, 6R)-Ethyl-2-acetamido-2-cyano-3,4--cyclohexylidenedioxybicyclo[3,1,0]hexane-6carboxylate
I Tetrahedron:Asymmetry1997,8, 51l
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal O
~CO2Et
E.e. > 98% [(z]D=-255 (cl .0, CH3OH) Source of chirality:D(+)-Ribonic7-1actone Absolute configuration:l R, 5S, 6S
C9H1003 (-)-(1 R, 5S, 6S)-Ethyl-4-oxobicyclo[3,1,0]-2-hexene-6-carboxylate
A94
I Tetrahedron:Asymmetry 1997, 8, 511
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
E.e. > 98%
0
[O[]D=+64.6 (C 1.0, CH3OH) Source of chirality:D(+)-Ribonic 7-1actone
~C02Et
Absolute configuration:l S, 5R, 6S
09H1203 (+)-(1 S, 5R, 6S)-Ethyl-2-oxobicyclo[3,1,0]-2-hexane-6-carboxylate
I Tetrahedron:Asymmetry 1997,8, 511
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal OC--NH I % HN,oo. =CO
E.e. > 98% [0~]D= -24 (C 0.5, MeOH)
~C02Et
Source of chirality:D(+)-Ribonic 7-1actone Absolute configuration:l S, 2S, 5R, 6S
C11H14N204 (-)-(1 S, 2S, 5R, 6S)-Ethyl bicyclo[3,1,0]hexane-2-spiro-5'-hydantoine°6-carboxylate
Tetrahedron: Asymmetry 1997,8, 511
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
E.e. > 98%
[e(]D=+74.0 (C 1.0, CHCI3)
O
H~o~CO2Et
Source of chirality:D(+)-Ribonic 7-1actone Absolute configuration:l S, 2R, 3R, 5S, 6S
C9H1205 (+)-(1 S, 2R, 3R, 5S, 6S)-Ethyl-2,3-dihydroxy-4-oxobicyclo[3,1,0]hexane-6-carboxylate
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
O,
E.e. > 98%
O
HO ' = ~ , , , m
Tetrahedron: Asymmetry 1997,8, 511
[C£]D=-49.5 (c 0.4, CHCl3) CO2Et
Source of chimlity:D(+)-Ribonic 7-1actone
HO" Absolute configuration:IS, 3R, 4R, 5R, 6S CllH1606 (-)-(lS, 3R, 4R, 5R, 6S)-Ethyl-2,2-ethylenedioxy-3,4-dihydroxybicyclo[3,1,0]hexane-6-carboxylate
A95
Tetrahedron: Asymmetry 1997, 8, 511
C. Dom[nguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal E.e. > 98%
O,
[OC]D= -204.6 (cl .15, CHCI3)
O
Source of chirality:D(+)-Ribonic y-lactone
"~CO2Et
Absolute configuration: 1R, 5S, 6S CllH1404 (-)-(1 R, 5S, 6S)-Ethyl-4,4-ethylenedioxybicyclo[3,1,0]-2-hexene-6-carboxylate
Tetrahedron: Asymmetry 1997, 8, 511
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
E.e. > 98% [C~]D=+37.7 (C 0.65, HCI 1N)
H 2 N ~ , ~CO2H
Source of chirality:D(+)-Ribonic y-lactone Absolute configuration:IS, 2S, 5R, 6S C8H1104 (+)-(lS, 2S, 5R, 6S)-2-aminobicyclo[3,1,0]hexane-2,6-dicarboxylic acid
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
HOO)~
Cf
[~]~0 + 6.8 (c 0.56, H20) Source of chirality: (R)-prolinol Absolute configuration: R CTHj4CIN02
R-3-(2-Pyrrolidinyl)propanoic acid hydrochoride
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
[a]~° + 31.5 (c 0.7, CHCI3) Source of chirality: (R)-prolinol Absolute configuration: R C7HI INO (R)- l-Azabicyclo[3.3.0]octan-2-one
A96
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
[tx]~° 20.1 (c 1.49, CH3OH) Source of chirality: (R)-prolinol Absolute configuration: R C20H33NO8
EtOOC BOC EtOOC COOEr
(2R)-2-[2-(N-tert-Butoxycarbonylpyrrolidinyl)]- 1,1,1-tris-(ethoxycarbonyl)ethane
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
[t~]~° -26.3 (c 0.8, CHCI3) Source o f chirality: (R)-prolinol Absolute configuration: R C7HgNO
O
(R)- l-Azabicyclo[3.3.0]oct-3-en-2-one
Tetrahedron: Asymmetry 1997, 8, 519 David M. Hodgson and Robert E. Marriott
Ee = 35% (by chiral HPLC of 3,5-DNB deriv, of corresponding endo-alcohol) [a]D 20 = -18 (c 1.0, CHCI3) Source of Chirality: Desymmetrisation of achiral epoxide C9H 14°
using lithium (S,S)-bis(l-phenyl)ethylamide Absolute configuration (tentative): 1S,4S,5S,6R
endo-cis-5,6-Dimethylbicyclo[2.2. I ]heptan-2-one
(assigned by analogy to products observed with exo- and endo-norbornene oxides)
Tetrahedron: Asymmetry 1997, 8, 519 David M. Hodgson and Robert E. Marriott
Ee = 32% (by chiral HPLC of 3,5-DNB deriv, of corresponding endo-alcohol) [a]D 2° = +8 (c 0.5. CHCI3) Source of Chirality: Desymmetrisation of achiral epoxide C7HtoO
using lithium (S,S)-bis( l-phenyl)ethylamide Absolute configuration: IS,4R
Bicyclo[2.2. I ]heptan-2-one
(assigned by comparison of sign of [aid of ketone with lit.)
A97
I Tetrahedron:Asymmetry 1997,
David M. Hodgson and Robert E. Marriott
8, 519
Opticalpurity= 19% [O~]D20 = -99 (c 0.5, CHCI3) Source of Chirality: Desymmetrisation of achiral epoxide using lithium (S,S)-bis(I-phenyl)ethylamide
CsHioO
Absolute configuration: IS,4S Bicyclo[2.2.2]oct-5-en-2-one
(assigned by comparison of sign of [or]o of ketone with lit.)
I Tetrahedron:Asymmetry 1997,
J. A. Hyatt and Chad Skelton
TBDMS-O~
8, 523
E.e. = > 95% (chiral column HPLC) mp = 60-65 ° [C~]24 D : + 14.7 (C = 0.42, CHCI3) Absolute configuration: 2S Source of chirality: Enzyme-catalysed kinetic resolution
cH°
Tetrahedron: Asymmetry 1997, 8, 523
J. A. Hyatt and Chad Skelton
0
HO~o CH20~CO2H
E.e.=96.5% (chiral-column HPLC) mp 97-100 ° [ot]24o= +0.48 (0.50, CHCI3) Absolute configuration 2S Source of chirality: Enzyme-catalysed kinetic resolution
(S)-6-Hydroxy-2,5,7,8-tetramethyl-2chromanmethanol succinate
Tetrahedron: Asymmetry 1997,
J. Meiwes, M. Schudok, G. Kretzschmar
BrH2~NCOzH
E.e. > 9 9 . 8 % ( O P A derivatization and I-IPLC) [oq20 = -29.3 ( c = l , H 2 0 ) Source ofehirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C7HsBrNO2S L-3-(4-bromo-2-thienyl)alanine
A98
8, 527
Tetrahedron: Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
Cl'laH2~CO2 H
E.e. >99.8% (OPA derivatization and HPLC) [t~]20 = -19.6 (c=l, H20 ) Source ofchirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C8H1 INO2 S L-3-(5-methyl-2-thienyl)alanine
I Tetrahedron:Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
CO2H NH2
E.e. >99.8% (OPA derivatization and HPLC) [OQ2D 0 =-38.9 (c=l, n20) Source of chirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C7H9NO2S L-3-(3-thienyl)alanine
Tetrahedron: Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
H2~CO2 H
E.e. >99.8% (OPA derivatization and HPLC) [=1~° = - 3 0 . 3 ( c = l , H20) Source ofchirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C7H9NO2S L-3-(2-thienyl)alanine
Tetrahedron: Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
CHs
E.e. >99.8% (OPA derivatization and HPLC) [t~]20 = -8.8 (c=l, 1N NaOH)
H2~N~ CO2H
Source ofchirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C8H11NO2S L-3-(3-methyl-2-thienyl)alanine
A99
M. Smr~ina,* S. Vysko~il, J. Polfvkovti, J. Pol~kov~, J. Sejbal, V. Hanu§, M. Pol,~§ek, H. Verrier, and P. Ko(~ovsk3/*
I
I
Tetrahedron: Asymmetry 1997, 8, 537
E.e. 97% [by chiral HPLC] mp 158-160 °C (EtOH or petroleum ether-CH2CI2) OCSNMe2 [a]o -154 (c 0.1, CHCI3) or -111 (c 1.0, THF) [ ~ OCSNMe2 Source of chirality: (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl (BINOL) Absolute configuration: S 026H24N202S2 (assigned by genetic relation to BINOL) 2,2'-Di[(N,N-dimethylthiocarbamoyl)oxy]-1,1'-binaphthyl
M. Smr(Sina,*S. Vysk06il, J. Polfvkowl, J. Poh~kov~i,J. Sejbal, V. Hanu.~,M. Pol~i.~ek,H. Verrier, and P. Ko6ovsk3/*
I
I
Tetrahedron: Asymmetry 1997, 8, 537
E.e. >99% [by chiral HPLC] mp 183-184 °C (MeOH) OCSNMe2 [~(]D-144 (C 0.5, CHCI3) [ ~ SCONMe2 Source of chirality: (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl (BINOL) Absolute configuration: S 026H24N202S2 (assigned by genetic relation to BINOL) 2-[(N,N-dimethylthiocarbamoyl)oxy]-2'-[(N,N-dimethylcarbamoyl)mercapto]-1,1'-binaphthyl
M. Smn~ina,* S. Vysko~il, J. Polfvkov~,J. Pola.kov~,J. Sejbal, V. Hanu§, M. Pol~i.~ek,H. Verrier, and P. Ko~ovsk3/*
SH
020H140S 2-Hydroxy-2'-mercapto-1,1 '-binaphthyl
E.e. > 98% [by 1H NMR of the derivative with (-)-menthyl chloroformate] [a]D +5.7 (c 0.9, EtOH) Source of chirality: (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl (BINOL) Absolute configuration: S (assigned by genetic relation to BINOL)
M. Smr~ina,* S. Vysko6il, J. Polfvkov~,J. Pol~ikov~i,J. Sejbal, V. Hanu~, M. Pol~i~ek,H. Verrier, and P. Ko~ovsk~;*
~
NHCOCH 3 OH
022H17NO2 2-(Acetamido)-2'-hydroxy-1,1'-binaphthyl
Tetrahedron: Asymmetry 1997, 8, 537
Tetrahedron: Asymmetry 1997, 8, 537
E.e. >99% [by chiral HPLC] mp 208-208.5 °C (EtOH) [Ct]D-79 (C 0.5, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydmxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
A100
Tetrahedron: Asymmetry 1997, 8, 537
v
M. Smrcina,* S. Vysko~il, J. Polfvkov~i,J. Pol~kov~, J. Sejbal, V. Hanu§, M. Polfi.~ek,H. Verrier, and P. Ko~ovs~ *
~
NHCOCH 3 OCOCH3
024H19NO3 2-(Acetamido)-2'-acetoxy-1,1'-binaphthyl
mp 162-163 °C (MeOH) [cx]o-88 (c 1, CHCla) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
I
Tetrahedron: Asymmetry 1997, 8, 537 M. Smr~ina,* S. Vyskot~il,J. Polfvkov~,J. Polfikovfi, J. Sejbal, I V. Hanu~,, M. Pol~.~ek, H. Verrier, and P. Ko~ovsk~ * [ ~ E.e. >99% [by chiral HPLC] mp 66-68 °C (n-heptane) NHCOCH3 [aiD -20 (C 0.5, CHCI3) OCSNMe2 Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S 02sH22N202S (assigned by genetic relation to NOBIN) 2-(Acetamido)-2'-[(N,N-dimethylthiocarbamoyl)oxy]-1,1'-binaphthyl
M. Smrdina,* S. Vysko~il, J. Polfvkov~,J. Polfikovfi, J. Sejbal, V. Hanu.~,M. Pol~.~ek,H. Verrier, and P. Ko~ovsk~ *
~
NHCOCH3 SCONMe2
I
I
Tetrahedron: Asymmetry 1997,
8, 537
E.e. >99% [by chiral HPLC] [~]D -190 (C 0.5, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
C25H22N202S 2-(Acetamido)-2'-[(N,N-dimethylcarbamoyl)mercapto]-I,1'-binaphthyl
I Tetrahedron:Asymmetry 1997, 8, 537 M. Smr~ina,* ,~. Vysko~U,J. Poffvkovd.,J. Pol~kov~, J. Sejbal, V. Hanu~,, M. Pol~§ek, H. Verrier, and P. Ko~ovsk~ * E.e. >97.4% [by chiral HPLC of its hydrobromide] mp 127-131 °C (dec; EtOH) NH2 [tZ]o +19 (c 0.1, CHCI3) SH Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN) C2oH15NS 2-Amino-2'-mercapto-1,1'-binaphthyl
~
AIOI
Tetrahedron: Asymmetry 1997,
8, 537
M. Smr~ina,* S. Vysko~il, J. Polrvkov~,J. Pol~kov~, J. Sejbal, V. Hanu.~,M. Pol~§ek, H. Varrier, and P. Ko~ovslo~* [ ~ E.e. >99% [by chiral HPLC] mp 194-194.5 °C (toluene) NMe2 [a]D -32.6 (C 1, THF) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN) C22H19NO 2-(N,N-Dimethylamino)-2'-hydroxy-1,1'-binaphthyl
@°"
Tetrahedron: Asymmetry 1997, 8, 537 M. Smr~ina,* ,S. Vysko6il, J. Polrvkov~[,J. Poi~kowl, J. Sejbal, V. Hanu§, M. Pol~§ek, H. Verrier, and P. Ko~ovsk9 * E.e. 98.2% [by chiral HPLC] [ ~ mp 120-122 °C (CH2CI2-heptane) NMe2 [ct]D -8.8 (c 1, THF) OCSNMe2 Source of chiral~y: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S C25H24N2OS (assigned by genetic relation to NOBIN) 2-(N,N-Dimethylamino)-2'-[(N,N-dimethylthiocarbamoyl)oxy]-1,1'-binaphthyl
Tetrahedron: Asymmetry 1997,
M. Smr~ina,* ,~. Vysko6il, J. Polrvkovd,J. Pol~.kov~,J. Sejbal, V. Hanu.~,M. Pol~§ek, H. Verrier, and P. Ko~ovslo~*
~
NMe2
SCONMe2
8, 537
[Ct]D-25 (C 0.4, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
025H24N2OS 2-(N,N-Dimethylamino)-2'-[(N,N-dimethylcarbamoyl)mercapto]-1,1'-binaphthyl
I
"Asymmetry 1997,
8, 537
M. Smr~ina, S. Vysko~il, J. Polrvkovd,J. Pol~kov~i,J. Sejbal, V. Hanu§, M. Pol,~§ek,H. Verriar, and P. Ko~ovsk~ * E.e. 96.2% [by chiral HPLC] mp 124-126 °C (toluene-petroleumether 1:1) NMe2 [a]O -27 (C 0.4, THF) SH Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBINI Absolute configuration: S (assigned by genetic relation to NOBIN) C22H19NS 2-(N,N-Dimethylamino)-2'-mercapto-1,1'-binaphthyl
~
A102
M. Smr~ina,* S. Vysko~il, J. Polfvkov~, J. Pol~kov~;, J. Sejbal, V. Hanu.~, M. Pol~ek, H. Verrier, and P. Ko~.ovs~ *
~
NMe
Tetrahedron: Asymmetry 1997, 8, 537
E.e. 52.8% [by ehiral HPLC] [cold+114 (c 0.4, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1 '-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
C22H15NOs
Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Novak and L. Poppe HO~OAc O-~- O
I
I
CsH 1~,O5 3-hydroxy-2-acetoxymethylpropanal dimethyl acetal
E.e.= 44% [~H-NMR of MTPA ester] 12(} a]~ = +4.1 (c=l, acetone) Source ofchirality: enzymatic acetylation Absolute configuration: R (assumed by analogy with the other members of the series)
Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Novak and L. Poppe H O ~ O_A c
J
O1"~O
L.
E.e.= 71% [tH-NMR of MTPA ester ] [oriel'= +4.9 (c=l, acetone) Source of chirality: enzymatic acetylation
C BoH2oO5 3-hydroxy-2-acetoxymethylpropanal diethyl acetal
Absolute configuration: R (determined by chemical transformation into a compound with known absolute configuration)
I Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Novb.k and L. Poppe HO.-"~f,'~OAc
E.e.= 68% [IH-NMR of MTPA ester] [ot]t~i'=+3.7 (c=l, acetone) Source ofchirality: enzymatic acetylation
CI6H3205 3-hydroxy-2-acetoxymethylpropanal di-i-amylacetal
Absolute configuration: R (assumed by analogy with the other members of the series)
A103
Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Nov~ik and L. Poppe HO.,."',,,z,,,"~ OA c
E.e.= 70% [IH-NMR of MTPA ester] [ot]l:i)=+7.4 (c=l, acetone)
O.J'-,O
Source ofchirality: enzymatic acetylation
C20H2405 3-hydroxy-2-acetoxymethylpropanal dibenzylacetal
Absolute configuration: R (assumed by analogy with the other members of the series)
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o -.o
I Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(~]D22= +35 (C = 2.0 in CHC13)
~OCPh3
Source of chirality: synthesis from natural product
C)H C2sH2sO4
Absolute configuration: 2R, 4S, 5R
2-Methyl-4-(trityloxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
J--o L~-~.OC
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
H2Ph
OH C~3H1804
[(~.]D22 = -----0.5(C = 3.9 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
2-Methyl-4-(benzyloxymet~yl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o.J-.o
L~OSitBuPh2 0
C221-t2804Si
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
[CI-]D22= - - 5 1 (c = 4.6 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S
2-Methyl-4-(t-butyldiphenylsilyloxymethyl)1,3-dioxan-5-one
A104
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o
~
E.e.
OCPh3
O 025H2404 2-Methyl-4-(b'ityloxymethyl)1,3-dioxan-5-one
=
[0~]D22
100% (by preparation method) =
----49.5 (c = 3.6 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o
L~CX~I-12Ph 0
C13H1BO4
Tetrahedron: Asymmetry 1997, 8, 559
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct.]D22 = --36 (c = 3.8 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S
2-Methyl-4-(benzyloxymethyl)1,3-dioxan-5.-one
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/1-.o L~ositBuPh2 0 022H2sO4Si 2-Methyl-4-(t-Ixltyldiphenylsilyloxymethyl)1,3-dioxan-5-one
E.e. = 100% (by preparation method) [0/,]D22 = +82 (c = 1.0 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o L~OCPh3 0 Czs~404
Tetrahedron: Asymmetry 1997, 8, 559
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [C[,]D22 = +51 (c = 2.6 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R
2-Methyl-4-(trityloxymethyl)1,3-dioxan-5-one
A105
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-.o L,~OCI..12 Ph 0 013H1604 2-Methyl-4-(benzyloxymethyl)1,3-dioxan-5-one
E.e. = 100% (by preparation method) [Ct]D22= +57 (C = 2.0 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R
M. Carda, P. Casab6, F. Gonz~ilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/1..o %L~oSitBuPh2 ~%OH C23H3204Si
Tetrahedron: Asymmetry 1997, 8, 559
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(X]D22 =
+14 (c = 3.5 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
2,5-Dimet~yl--4-(t-butyldiphenylsilyloxyme~yl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonz~ilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(X]D22 =
+5.4 (C = 1.1 in CHC6)
Source of chirality: synthesis from natural product C7H1404
Absolute configuration: 2R, 4S, 5R
2,5-Dimethyl-4-(hydroxymet~yl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o %L~OCI-~Ph %"OH C141-12oO4
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Gt,]D22 =
+20.5 (c = 1.8 in CHC13)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
2,5-Dirnethyl-4-(benzyloxymethyl)1,3-dioxan-5.-ol
A106
M. Carda, P. Casab6, F. Gonz~ez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/i--o ~'OH C2e~804 2,5-Dimethyl-4-(trityloxyrnethyl)1,3-dioxan-5-ol
E.e. = 100% (by preparation method) [ot]t)z2= +4.7 (c = 5.1 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and JA. Marco. OH J'~ A /OCH2Ph HO" ~"OH v
Tetrahedron: Asymmetry 1997, 8, 559
I Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [0£]D22 = ---8.2 (c = 1.5 in CHCI3)
Source of chirality: synthesis from natural product C12HlsO4 4-O-Benzyl-2-rnethylbutane-1,2,3,4-te'o'aol
Absolute configuration: 2R, 3S
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A Marco. .OCH2Ph ~ /OCH2Ph PhCH20" /%"OH v
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D22= +10.2 (C = 6.0 in CHCI3) Source of chirality: synthesis from natural product
C261-1~O4 1,3.4-Tri-O-benzyl-2-meth~bul~lne-1,2,3,4-tetraol
Absolute configuration: 2R, 3S
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o 1.. o
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
_ ..L~ ~OSitBuph2
[G£]D22 = - - 5 . 6 (c = 2.5 in CHCI3)
"'/%OH
Source of chirality: synthesis from natural product
C241"13404Si
Absolute configuration: 2R, 4S, 5R
5-Ethyl-2-methyl-4-(t-butyldiphenylsilyloxymethyl)1,3-dioxan-5-ol
AI07
M. Carda, P. Casab6, F. Gonz/dez, S. Rodriguez, L.R. Domingo and J.A. Marco.
Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [a]o22 = - - 1 3 . 0 (c = 5.6 in CHC13) Source ofchirality: synthesis from natural product Absolute configuration: 21L 4S, 5R
CaHlsO4 5-Ethyl-2-methyl-4-(hydroxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/1-.o ~% ~
I Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
OCH2ph
[ct]o22 =--2.1 (c = 1.4 in CHCI3)
Source of chirality:synthesisfrom naturalproduct ClsH2204
Absolute configuration:2R, 4S, 5R
5-Ethyl-2-rnet~yl-4-(benzyloxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonz/dez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I--o ~"~'OH C27H3004
I Tetrahedron:Asymmetry 1997, &
559
E.e. = 100% (by preparation method) [ct]022 =----3.6 (c = 5.5 in CHC13) Source of chirality: synthesis from natural product Absolute configuration: 21L 4S, 5R
5-Ethyl-2-methyl-4-(tdtyloxyrnethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco. Old
Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D22= --11.5 (C = 0.34 in CHCh) Source of chirality: synthesis from natural product
C13H2004 4-O-Benzyl-2-ethylbutane-1,2,3,4-tetTaol
Absolute configuration: 2R, 3S
AI08
M. Carda, P. Casab6, F. Gonz~ez, S. Roddguez, L.R. Domingo and J.A. Marco.
~ p hCI.-~O . ~ , , O H
.OCI.-12Ph /OCI'I2Ph Y
Tetrahedron:Asymmetry1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D22= +9.0 (C = 2.6 in CHCI3) Source of chirality: synthesis from natural product
C2d-13~4 1,3.4-Tri-O-benzyl-2-ethylbutane-1,2,3,4-teU'aol
Absolute configuration: 2R, 3S
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-~
Tetrahedron:Asymmetry1997, 8, 559
Ee. = 100% (by preparation method) OSitBuPh2
[C¢.]D22= +8.8 (c = 5.5 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
C23H3204Si 2,5-Dimethyl..4-(t-butyldiphenylsilyloxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and JA. Marco.
oJ-._o
I Tetrahedron:Asymmetry1997, 8, 559
E.e. = 100% (by preparation method) [ct]022 = +17.0 (c = 0.8 in CHC13) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
C7H1304 2,5-Dimethyl-4-(hydroxymethyl)1,3.-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-. ~
I Tetrahedron:Asymmetry1997, 8, 559
E.e. = 100% (by preparation method) OCH2Ph
C14H~O4
[ff,]D 22 =
+15.5 (c = 1.6 in CHC13)
Source ofchirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
2,5-Dime~yi-4-(benzyloxymethyl)1,3.-dioxan-5.-ol
A109
M. Carda, P. Casab6, F. Gorghlez, S. Rodriguez, L.R. Domingo and JA. Marco.
1.o ~
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) OCPh3
/'"OH
026H2804 2,5-Dimethyl-4-(ttityloxymethyl)1,3-dioxan-5-ol
[Ct]D22= +5.5 (C = 1.9 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco. QH
/~...~ /OCH2Ph HO" ~"OH v
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [a]D 22= +6.4 (C = 1.1 in CHC13) Source of chirality: synthesis from natural product
C12H1804 4-O-Benzyl-2-me~ytbutane-1,2.3.4-tetraol
Absolute configuration: 2R, 3R
Tetrahedron: Asymmetry 1997, 8, 559 M. Carda, P. Casab6, F. Gonzalez, S. Rodfiguez, L.R. Domingo and J.A. Marco. ()CH2Ph A /OCH2Ph PhCH20" / " O H /~.
E.e. = 100% (by preparation method) [Ct]D22 = --2.6 (C = 0.4 in CHC13) Source of chirality: synthesis from natural product
c2d-~04 1,3.4-Tri-O-benzyl-2-methylbutane-1,2,3,4-tetraol
Absolute configuration: 2R, 3R
M. Carda, P. Casab6, F. Gonz~ilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
¢-o
_ ~O6itBuPh2
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D 22 =
+14.5 (c = 4.0 in CHCi3)
Source of chirality: synthesis from natural product C24H3404Si 5-Ethyi-2-met~yi-A-(t-butyldiphemylsilyloxyrnethyl)1,3-dioxan-5-ol
Absolute configuration: 2R, 4R, 5R
All0
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
J-o
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D:2= +17.5 (C = 0.7 in CHCI3) Source of chirality: synthesis from natural product
C8H1604 5-Ethyl-2-methyl-4-(hydroxymethyl)1,3-dioxan-5-.d
Absolute configuration: 2R, 4R, 5R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-.o
E.e. = 100% (by preparation method)
_ ~OCH2Ph "~'~"
Tetrahedron: Asymmetry 1997, 8, 559
[(X]D22 =
+18.5 (c = 1.6 in CHCI3)
Source of chirality: synthesis from natural product
" "OH
Absolute configuration: 2R, 41L 5R
ClsPe204 5-E~yl-2-methyl..4-(l~n zylo~o/n'~thyl)1,34ioxan-5-~l
M. Carda, P. Casab6, F. Gonzhlez, S. Rodfiguez, L.R. Domingo and JA. Marco.
oJ-.
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(g]D22 = +5.0 (c = 28 in CHCIs)
~'OH
Source of chirality: synthesis from natural product
C27H~04 5-E~yl-2-methyl-4-(tm'yloxymethyl)1,3-dioxan-5-ol
Absolute configuration: 2R, 4R, 5R
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, UR. Domingo and J.A. Marco. ~H
H O ~
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
OCH2Ph
[(X]D22 =
+6.5 (c = 1.5 in CHCI3)
Source of chirality: synthesis from natural product C1a~oO4
4-O-Benzyt-2-ethylbutane-1,2,3,4-tetraol
Absolute configuration: 2R, 3R
Alll
Tetrahedron:Asymmetry 1997, 8, 559
M. Carda, P. Casab6, F. Gonzfi/ez, S. Rodriguez, L.R. Domingo and J.A. Marco.
OCH2Ph P h C H 2 0 ~ OCH2Ph
E.e. = 100% (by preparation method) [CqD22= - - 9 . 3 (C = 0.1 in CHCh) Source of chirality: synthesis from natural product
C27He204
Absolute configuration: 2R, 3R
1,3.4-Td-O-benzyl-2-ethylbutane-1,2,3,4-tetraol
I
F. Dumas*, K. Aiencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa*
OH
"Asymmetry 1997,
8, 579
ee > 92 % [~]D 20= -51.9 (c = 1.9, EtOHabs) Source of chirality: (1S)-(-)-13-pinene (92 % ee) Absolute configuration: IR, 2R, 3S, 5R
CI6H220 3-Benzyl nopinol
l Tetrahedron:Asymmetry 1997,
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa*
OH MeO~~"~ C 17H24O 3-[(4-Methoxyphenyl)-methyl] nopinol
8, 579
ee > 92 % Mp 47 °C (pentane) [~]D20 = -25.3 (c = 1.74, EtOHab s) Source of chirality: (IS)-(-)-13-pinene (92 % ee) Absolute configuration: 1R, 2R, 3S, 5R
I Tetrahedron:Asymmetry 1997,
F. Dumas a*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconceilos*, P.R.R. Costa*
ee > 92 % [0£]020 = -30.9 (c = 2.1, EtOHab s) Source of chirality: (1S)-(-)-B-pinene (92 % ee) Absolute configuration: 1R, 2R, 3S, 5R C 17H24O
3-[(2-Methoxyphenyl)-methyl] nopinol i
All2
8, 579
J Tetrahedron:Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa*
ee > 92 % Mp 112 °C (pentane) [O~]D20 = -54.0 (c = 1.45, EtOHabs) Source of chirality: (1S)-(-)-13-pinene (92 % ee) Absolute configuration: IR, 2R, 3S, 5R
C20H240 3-[( 1-Naphthyl)-methyl] nopinol
J Tetrahedron:Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa* OH
ee > 92 % [(/.]D20 = -11.4 (c = 1.8, EtOHabs) Source of chirality: (lS)-(-)-8-pinene (92 % ee) Absolute configuration: 1R, 2R, 3S, 5R
C20H24O 3-[(2-Naphthyl)-methyl] nopinol
Tetrahedron: Asymmetry 1997, 8, 579 F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa* OH
C 16H22O 3-Benzyl nopinol
ee > 92 % Mp 110 °C (Et20:pentane 1:1) [O~]D20 ---- -42 (c = 2, EtOHabs) Source of chirality: (IS)-(-)-13-pinene (92 % ee) Absolute configuration: 1R, 2S, 3S, 5R
Tetrahedron: Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa* OH
C17H24O
3-[(4-Methoxyphenyl)-methyl] nopinol
ee > 92 % Mp 112 °C (pentane) [0~]D20 = -51.6 (C = 1.4, EtOHa~) Source of chirality: (IS)-(-)-B-pinene (92 % ee) Absolute configuration: 1R, 2S, 3S, 5R
All3
Tetrahedron: Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. GErard, M.L. Vasconcellos*, P.R.R. Costa* OMe
ee > 92 % [ct]o2° = -57.3 (c = 1.5, EtOHabs) Source of chirality: (1S)-(-)-B-pinene (92 % ee) Absolute configuration: IR, 2S, 3S, 5R
OH
C17H240 3-[(2-Methoxyphenyl)-methyl] nopinol
Tetrahedron: Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. GErard, M.L. Vasconcellos*, P.R.R. Costa* O
+
ee = 92 % [ot]D2° = + 17.6 (neat) Source of chirality: (1S)-(-)-f3-pinene (92 % ee) Absolute configuration: IS, 5S
C9H 14° Nopinone
Tetrahedron: Asymmetry 1997, 8, 591
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard Ph
ee " 85% (by chiral HPLC analysis) [Ot]D =-91.9 (c 1%, MeOH-HCI) CIsHI7NO (R)-(-)- l-(4-methoxyphenyl)-2-phenylethylamine
Tetrahedron: Asymmetry 1997, 8, 591
P. Moreau, M. Essiz, J.Y. MErour and D. Bouzard
H2S© Ph
ee ' 94% (by chiral HPLC analysis) [Ct]D =-118 (c 1.01%, MeOH-HCI) [OqD = -10.1 (c 1.34%, CHCI3)
CI4H15N R-(-)- 1,2-diphenylethylamine
All4
Tetrahedron:Asymmetry1997,8, 591
P. Moreau, M. Essiz, J.Y. M6rour and D. Bouzard.
ee : 88% (by chiral HPLC analysis) [~]D =-4.4 (c 1.02%, MeOH-HCI) C18H17N (R)-(-)- 1-(1)-naphtyl-2-phenylethylamine
l Tetrahedron:Asymmetry1997, 8, 591
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard Ph
ee: 77% (by HPLC chiral analysis) [Ct]D =-117 (c 1.02%, MeOH-HCI) C 14I-I14CIN (R)-(-)- l-(4-chlorophenyl)-2-phenylethylamine
I Tetrahedron:Asymmetry1997,
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard
8, 591
Ph ee : 84% (by chiral HPLC analysis) [~t]D =-95 (c 1.01%, MeOH-HC1)
c ~20N2 (R)-(-)- l-(4-dimethylaminophenyl)-2-phenylethylamine
I Tetrahedron:Asymmetry1997, 8, 591
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard.
ee : 75% (by chiral HPLC analysis) cto = -43.5 ° (c 1%, MeOH-HCI) ee > 99% (by chiral HPLC analysis) [Ct]D = -94 (c 1.01%, MeOH-HCI) C21H21NO (R)-(-)- 1-(2-benzyloxyphenyl)-2-phenylethylamine
All5
Tetrahedron: Asymmetry 1997, 8, 599
ValmtinaFAVERO,OimniI~RZI E ! S¢~gioSANDRI
[a] ~= -297.7 (c= 2.5, chloroform)
Source of chirality : (S)-phenylethylamine Absolute configuration : 6R, I'S assigned by 1H-NMR C13H16N202
(6R, l'S)-l-(l'-Phenethyl)-6-methyl-piperazine-2,5-dione
I
ValmlimFAVERO, GianniPORZIand SmgioSANDRI
: Asymmetry 1997, 8, 599
[a]~= 37.8 (c= 2.13, chloroform) IJ Source of chirality: (S)-phenylethylamine Absoluteconfiguration: 6S,I'S assignedby IH-NMR C13H16N202
(6S,1 'S)- 1-( 1'-Phenethyl)-6-methyl-piperazine-2,5-dione
Tetrahedron: Asymmetry 1997, 8, 599
ValenfinaFAVERO,GianniPORZIsad SergioSANDRI )C2Hs
CH~ [a]~= -288.4 ( ~ 2.71, chloroform) L,P Source of chirality : (S)-phenylethylamine Absolute configuration : 6R, I'S assigned by 1H-NMR C15I-I20N202
CH 3 0
(6R, l'S)-l-(l'-Phenethyl)-5-ethoxy-6-methyl-3,6-dihydro-lH-pyrazine-2-one
I Tetrahedron:Asymmetry 1997, 8, 599
ValentinaFAVERO.GiaaniPORZIand SergioSANDRI
{I)C2H$ [a]~= 37.5 ( ~ 2.1, chloroform) Source of chirality : (S)-pimnylethylamir~ Absolute configuration : 6s, r s assigned by 1H-NMR CI5H20N202
(6S,l'S)-l-(l'-Phenethyl)-5-ethoxy-6-methyl-3,6-dihydro-lH-pyrazine-2-one
All6
I Tetrahedron:Asymmetry1997, 8, 599
Vakalina FAVERO,GialmiPORZIand Sa'gio SANDRI
tit
I-Is
[a,]~= -5.1 ( ~ 8.4, chloroform) S o u ~ of chirality : (S)-pbcnylethylamin¢ Absolute configuration : 31L6S,1'S assigned by 1H-NMR C20H28N202
CH3 0
(3•L6S•••S)••-(•••phenethy•)•5-eth•xy•3-(3•methy•-2•buteny•)-6-methy••3•6-dihydr•-•H-pyrazine•2••ne
Tetrahedron:Asymmetry1997, 8, 599
ValentinaFAVERO,Gianni PORZI and SczgioSANDRI
|
II CH~
CH3
[¢z]~=-16 (c= 4.8, chloroform) Sou~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H-NMR C20H28N202
O
(3S,6S, 1•S)-•-(•'-Phenethy•)-5-eth•xy-3-(3-methy•-2-buteny•)-6-methy•-3•6-dihydr•-•H-pyrazine-2-•ne
I Tetrahedron:Asymmetry1997, 8, 599
ValentinaFAVERO,Gianni PORZI and SergioSANDRI
C2Hs phCH~
CH3
[¢x]_25=40.3 (c= 2.2, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR C18H26N202
CH3 0 (3R,6S,1 'S)- 1-( 1'-Phenethyl)-5-ethoxy-3-isopropyl-6-methyl-3,6-dihydro- 1H-pyrazine-2-one
I Tetrahedron:Asymmetry1997, 8, 599
ValmfinaFAVERO,Gianni PORZI and Sergio SANDRI
C2Hs
[a]~= 17.1 ( ~ 3.7, chloroform) S o u ~ of ehirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by IH-NMR C18H~N202
3 (3R,~,l'S)-l-(l'-~yl)-5-etl~]-3-allyl-~me.Ihyl-3,f~tglydm-!H-p~2~
All7
Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIandSel'gioSANDRI
[~]~-- -14.3 (c= 0.5, chloroform) D Source of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H-NMR C18H24N202 3
(3S•6S•••S)•••(•'•Phenethy•)-5-eth•xy-3•a••y•-6-methy•-3•6-dihydr•-•H•pyrazine-2-•ne ValentinaFAVERO,GianniPORZIand~ )C2Hs
Ph
, N!," ~ .31/
Ph
Tetrahedron: Asymmetry 1997, 8, 599
SANDRI
[a]_25= -209.1 (c= 3.1, chloroform) Source of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C22H26N202
(35,6R, l'S)- 1-(l'-Phene~yl)-5--e~oxy-3-benzyl-6-me~yl-3,6-dihydm-1H-pyrazine-2-one I Tetrahedron:Asymmetry 1997, 8, 599
ValeatlnaFAVERO,GianniPORZIand SergioSANDRI
~C~Hs
[ix]_25=-237 (e= 1.9, chloroform) D Source of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR
Ph~cHN ~ ' ~ C H 3
CI8H26N202
3
(3S,6R, 1'S)- 1-( 1'-Phenethyl)-5-ethoxy-3 -propyl-6-methyl-3,6-dihydro-1H-pyrazine-2-one Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIandSergioSANDRI
p
N
CH3
[0t]25= -256 (e= 1.4, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C16I-I22N202
(3S,6R, l'S)-l-(l'-l:~nethyl)-5--ethoxy-3,6-dime~yl-3,6--dihydro- 1H-pyrazine-2-one
All8
Tetrahedron: Asymmetry 1997, 8, 599
ValeatinaFAVERO,GiaaniPORZIand Se~gioSANDRI )C2Hs
[¢x]p= -132.8 (c= 2.4, chloroform) S o u ~ of ehirality : (S)-phenylethylamine Absolute configuration : 3R,6R, I'S assigned by 1H-NMR CIsH24N202
CH 3 0
(3R,6R, I'S)- 1-(l'-Phenethyl)-5-ethoxy-3-allyl-6-methyl-3,6-dihydro-lH-pyrazine-2-one I Tetrahedron:Asymmetry 1997, 8, 599
ValeatinaFAVERO,GianniPORZ]and SergioSANDRI C2Hs
CH~ ~ . p h . ~ , N , ~
3
[a]25= -248.5 ( ~ 6.8, chloroform) Sou~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C]TH24N202
CH3 0 (3S•6R••'S)-•-(•'-Phenethy•)-5-eth•xy-3-ethy•-6-methy•-3•6-dihydr•-•H-pyrazine-2-•ne Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIand SergioSANDRI C2Hs
CH~.,
N
Ph-~N',~",f
CH3
[a]25= -132.6 (c= 1.8, chloroform) Sou°reeof chirality : (S)-phenylethylamine Absolute configuration : 3R,6R,I'S assigned by 1H-NMR CtTH24N202
CH 3 O
(3R,6R,I'S)- 1-(l'-Phenethyl)-5-ethoxy-3-ethyl-6-methyl-3,6-dihydro-lH-pyrazine-2-one Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO.GianniIK)RZIand SexgioSANDRI
~ C2Hs
cH3~, .,.~.
[a] 25=-211.2 (c= 11.4,chloroform) Source of chirality : (S)-phenylethylamine Absoluteconfiguration: 3S,6R, I'S assignedby IH-NMR C20H28N202
(3S,6R,l'S)-l-(l'-Phenethyl)-5-ethoxy-3-(3-methyl-2-butenyl)-6-methyl-3,6-dihydro1H-pyrazine-2-one
All9
Val~_0~ FAVERO,
I Tetrahedron:Asymmetry 1997,8, 599
Giarmi~3R2~ end SergioSANDRI
)C2H$ [(X]~= -268.4 (effi2.1, chloroform) S o ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR
ClsH26N202 (3S,6R,1~3)-1-(l'-Phenethyl)-5-ethoxy-3-isopropyl-6-methyl-3,6-dihydro-1H-pyr~zine-2-one
Al~sa~aMADAU,~ CH~.~.
Tetrahedron: Asymmetry 1997,8, 599
PORZIand S~o S/dDRI
IHs
[ct]~=-264.1 (c= 1.7, chloroform) Sou~r.e of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C18HuN202
(35,6R,1'S)- 1-(l'-Phene~yl)-5-ethoxy-3-allyl-6-me~yl-3,6-dihydm- 1H-pyrazine-2-one Tetrahedron: Asymmetry 1997,8, 599
ValentinaFAVERO,GianniPORZIandSergioSANDRI
•C2Hs
C
p
, N
CH3
[~]25= 18.2 (c= 0.9, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR
CI6H22N202
(3R,6S, l'S)-l-(l'-l:~ene~yl)-5--ethoxy-3,6-dime~yl-3,6-d~ydm- ltt-pyrR~ne-2-one ValesuinaFAVERO, GianniIK)RZl and
C2Hs
CIt,N ~
I Tetrahedron:Asymmetry 1997,8, 599
SergioSANDRI
[~]~= -20.3 (e= 2.2, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H-NMR CI6H22N202
(3S,6S,l'S)-l-(l'-P~ae~yl)-5-ethoxy-3,6-dime~yl-3,6-dihydm-lH-p~-2..one
AI20
V ~
FAVERO, Oiaam PORZI sml S ~
I Tetrahedron:Asymmetry1997, 8, 599
SANDRI
[Ct]~= -184.7 (c= 3.7, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3R,6R,1'S assigned by 1H-NMR p
, N
s
CH3
CI6I-I~N202
(3R,6R, I'S)- 1-(l'-Pl~ne~yl)-5-e~oxy-3,6-dime~yl-3,6-dihydm- 1H-pyrazine-2-one
I Tetrahedron:Asymmetry1997, 8, 599
ValeatinaFAVERO, OiamniFORZI and S~rgioSANDRI
C2Hs
[a]~= 156.8 (e= 1.5, chloroform) Source of chirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR
C22H~'~202 (3R,6S,l'S)-l-(l'-Phone~yl)-5-ethoxy-3-benzyl-6-methyl-3,6-dihydm- 1H-py~ziqe-2-one
VsdealinaFAVERO,~ C2Hs
I Tetrahedron:Asymmetry1997, 8, 599
PORZIand SetgioSANDRI
[tz]~= 19.6 (e= 0.4, chloroform) Source of ehirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR
CmH~',1202 CH 3 0
(3R,6S, 1'S)- 1-( 1'-Phenethyl)- 5-ethoxy-3 -propyl-6-methyl- 3,6-dihydro- 1H-pyrazine-2-one
Tetrahedron:Asymmetry1997, 8, 599
ValeatiaaFAVERO, GianniPORZI aad Seqio SANDRI
[a]~= -20.8 (c= 1, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H.NMR
CmH~I202 CHa O (3S,6S,1 'S)- 1-( 1'-Phenethyl)- 5-ethoxy-3-propyl-6-methyl-3,6-dihydro- 1H-pyrazine-2 -one
AI21
Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO, Oi~nl PO~Zl and Se~io SANDRI
? C21ts
cH,,,...,k.
CH3
[oq~= -32 (c= 2.8, chloroform) D Source of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R assigned by 1H-NMR CI2H20N202
(3S,6R)-5-ethoxy-3-(3-methyl-2-butenyl)-6-methyl-3,6-dihydro-lH-pyrazine-2-one Tetrahedron: Asymmetry 1997, 8, 599
ValenfinaFAVERO,GianniPORZIand SergioSANDRI
~ C2H5
CH~, I~.
[cx]_25=23.3 (c= 2.4, chloroform) S o u ~ of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R assigned by 1H-NMR C14HIsN202
0
(3S,6R)-5-ethoxy-3-benzyl-6-methyl-3,6-dihydro-lH-pyrazine-2-one I Tetrahedron:Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIand SergioSANDRI CH3 ,,, / C O O C 2 H s ' " ( C H 22C H =. C (~C H 3 )
H/N'~" NH3+CI"
[oq25= 28.9 (c= 3.1, chloroform) Sot~ce of chirality : (S)-phenylethylamine Absolute configuration : 2R,5S assigned by 1H-NMR C12H23C1N203
(2R,5S)-2-methyl-5-amino-3-aza-4-oxo-8-methyl ethyl-7-nonenoate hydrochloride Tetrahedron: Asymmetry 1997, 8, 599
Valentina FAVERO, Giaani PORZI and Sergio SANDRI
CH3,,,~/COOC2Hs "f ~HlPh HtN~NHCOCH3
[(x]25= -7 (c = 1.07, chloroform) LI Source of chirality : (S)-phenylethylamine Absolute configuration : 2R,5S assigned by 1H-NMR C16H22N204
(2R,5S)-2-methyl-5-acetamido-3-aza-4-oxo-6-phenyl ethyl-hexanoate
A122
ValeatinaFAVERO,Gianai~)RZIandSefgioSAN'DR/
Tetrahedron: Asymmetry 1997,
8, 599
[o.]_~= 37.1 ( ~ 2.9, chloroform) Sott~ee of ehirality : (S)-ethyl lactate Absolute configuration : 6R assigned by 1H.NMR
CH3N ~ N I H
CI2HI4N202 (6R)-1 -N-Benzyl-6-rnethyl-piperazine-2,5 -dione
ValenlinaFAVERO,GianniPORZIandSetgioSANDRI
I Tetrahedron:Asymmetry 1997, 8, 599
[or]25= -22.5 (c= 2.9, chloroform) D Source of chirality : (S)-ethyl lactate Absolute configuration : 6R assigned by 1H-NMR
CH3~,...~N H5
C14H18N202
Ph
0
(6R)-l-N-Benzyl-5-ethoxy-6-methyl-3,6-dihydro- 1H-pyrazine-2-one
I Tetrahedron:Asymmetry 1997, 8, 619
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
CH2\ / COOCH2OH3 /C. OH 2
NH 2
(+)-(S)-2',1': 1,2;l",2":3,4-Dinaphthcyclohepta-l,3-diene-6-amino-6-carboxylic acid ethyl ester. C26H23NO 2. [0~]25589 = +316.6, [(~]25578 = +331.1, [ec]25546 = +376.8, [0~]25436 = +603.3, [0~]25365 = +306.2 (c 0.5; MeOH).
Tetrahedron: Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
CH2
NH 2
(+)-(S)-2', 1': 1,2; 1" , 2 " :3,4-Dinaphthcyclohepta- 1,3-diene-6-amino-6-carboxylic acid tertbutyl ester. C28H27NO2. [(z]25589 = +309.8, [(x]25578 = +324.0, [(z]25546 = +368.4, [e~]25436 = +590.4 (c 0.5; MeOH).
A123
8, 619
Tetrahedron: Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~)avrdaand M. Wakselman
~
8, 619
O-12\ /COOH CH~"C~NH2
(+)-(S)-2', 1 ': 1,2; 1",2":3 ,4-Dinaphthcyclohepta- 1,3-diene-6-amino-6-carboxylic acid. C24HI9NO2. [~]25589 = +314.3, [~]25578 = +327.9, [5]25546 = +375.0, [a] 25436 = +616.7, [~]25365 = +423.3 (c 0.6; MeOH).
Tetrahedron: Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~)avrdaand M. Wakselman
8, 6 t 9
C. c C°°C.2C.3 CH2
NHCOOC(CH3) 3
(+)-(S)-2', 1': 1,2;1",2" 3,4-Dinaphthcyciohepta- l 3-diene-6-tert-buty]oxycarbonylan~no-6carboxytic acid ethyl ester. C31H31NO4. [o{]25589 = +38.5, [oc]25578 = +39.3, [c~]25546 = +41.0, [0~]25436 = -0.1, [0~]25365 = -599.7 (C 0.6; MeOH).
I Tetrahedron:Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
8, 619
CH2\ /COOC(CH3)3 jC\ OH2 N H(X~,(CH3 )3
(+)-(S)-2', 1' : 1,2; 1 " , 2 " :3,4-Dinaphthcyclohepta- 1,3-diene-6-tert-butyloxycarbonylarmno-6carboxylic acid tert-butyl ester. C33H35NO4. [o~]25589 = +38.7, [(z]25578 = +39.0, [0t]25546 = 25 4-41.0, [0[] 436 = -2.8, [~]25365 = -601.5 (c 0.5; MeOH).
Tetrahedron: Asymmetry 1997, 8, 619
J.-P. Mazaleyrat, * A. Gaucher, J. ~)avrdaand M. Wakselman
CH2
NH(XX)(~aC0H s
(+)-(S)-2', 1': 1,2; 1",2' ' :3,4-Dinaphthcyclohepta- 1,3-diene-6-benzyloxycarbonylamino-6carboxylic acid tert-butyl ester. C36H33NO4. [ct]25589 = +10.0, [1~]25578 = +9.5, [~]25546 = +6.6, [ff,]25436 -- -63.5, [o{]25365 = -684.4 (c 0.5; MeOH).
A124
I Tetrahedron:Asymmetry1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
CH2\ /CO(~ CH27C'NHCOOC(CH3)3
(+)-(S)-2', 1': 1,2; 1" ,2" :3,4-Dinaphthcyclohepta- 1,3-diene-6-tert-butyloxycarbonylanfino-6carboxylic acid. C29H27NO4. [t~]2%89 = +46.6, [ct]25578 = +47.6, [~]25546 = +50.2, [Ct]25436 +8.6, [1~]25365 = -644.6 (C 0.5; MeOH).
=
I[ Tetrahedron:Asymmetry1997, 8, 6 i 9
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
8, 619
Ct-12\ /1200t-I C H ~ C\NHCOOCH2C6H5
(+)-(S)-2', 1': 1,2; 1" ,2" :3,4-Dinaphthcyclohepta- 1,3-diene-6-benzyloxycarbonylamino-6carboxylic acid. C32H25NO4. [ct]25589 = +15.1, [~]25578 = +14.9, [(~]25546 = +12.9, [~]25 436 = 25 -56.0, [Ct] 365 = - 7 1 2 . 0 (c 0.5; MeOH).
I Tetrahedron:Asymmetry1997,
B. B. Lohmy * and S. Venkateawarlu
O
8, 633
= > 81% (determined based on optical rotation) [CqD21 = -31.5 (c, 0.5, CHCI3)
ee
~C10H21 i OAc
Source of chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 5R0 6S
(5R, 6 S)-6-Acetoxy-5-hexadecanolide
Tetrahedron:Asymmetry1997,
B. B. Lohray * and S. Venkatemwarlu
OMe
o
ee = 81% (determined based on optical rotation of final product) laiD 21 = -28.8 (c, 3.34, CHCI3) Source of chirality : Asymmetric dihydroxylation of corresponding olefin
ClcH21
Absolute configuration : 4S, 5S
(48, 5S)-4-Carbomethoxybutyl-5-decyl-l,3,2-dioxathiolane-2,2-dioxide
A125
8, 633
Tetrahedron:Asymmetry1997,
B. B. Lohmy * and S. Venlmteswarlu
8, 633
= c a . 8 1 % (determined based on optical rotation of final product) [aiD 21 = - 10.1 (C, 1.0, CHCI3)
ee
OM@
Source o! chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 5S, 6S
C~cH21 Methyl (5S, 6S)-5,6-dihydroxyhexadecanoate
I Tetrahedron:Asymmetry 1997, 8, 633
B. B. Lohray * and S. Venkateewadu
OMe
ee = ca. 8 1 % (determined based on optical rotation of final product) [(X]D21 = - 42.3 (C,1.0, CHCI3)
/(3
Source of chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 4S, 5S
CloH21
(4S, 5S )-Carbomethoxybutyl-5-decyl-1,3,2-dioxathiolane-2-oxide
I Tetrahedron:Asymmetry 1997, 8, 633 B. B. Lohray * and S. Venkateewarlu
O
~ C l o H 2 1 = OH (5R, 6 S)-6-hydroxy-5-hexadecanolide
ee = > 8 1 % (determined based on optical rotation) [aiD 21 = -12.5 (c, 0.54, CHCI3) Source of chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 5R, 6S
Tetrahedron:Asymmetry1997,
C.A.G.M. Weijers
E.e. > 98% (by GC analysis with a-Cyclodextrin column)
Source of chirality: Resolution by yeast epoxide hydrolase C9HI00
Absolute configuration: 1 R,2R
(1R,2R)-1-Phenyl- 1,2-epoxypropane
A126
8, 639
I
C.A.G.M. Weijers
H
Tetrahedron:Asymmetry 1997, 8, 639
OH E.e. > 98% (by GC analysis with 13-Cyelodextrin column) CH 3 [Ct]D24= - 32.8 (C = 0.6, CHC13) Source of chirality: Hydrolysis by yeast epoxide hydrolase
C9H 1202 (1R,2S)- l-Phenyl- 1,2-propanediol
Absolute configuration: 1 R,2S
I Tetrahedron: Asymmetry 1997, 8, 639
C.A.G.M. Weijers
E.e. > 98% (by GC analysis with ~t-Cyclodextrin column)
Source of chirality: Resolution by yeast epoxide hydrolase Absolute configuration: 1S,2R,4S C10HI60 (1S,2R,4S)-1,2-Epoxy-8-p-menthene
Tetrahedron: Asymmetry 1997, 8, 639
C.A.G.M. Weijers
~--
.... ,OH
E.e. > 98% (by GC analysis with 13-Cyclodextrin column)
Source of chirality: Hydrolysis by yeast epoxide hydrolase Absolute configuration: 1R,2R,4S C1oH1802 (1R,2R,4S)-8-p-Menthene- 1,2-diol
Tetrahedron: Asymmetry 1997, 8, 639
C.A.G.M. Weijers ,11IO
H3C
CsH10 O
'
E.e. > 98% (by chiral GC analysis)
-:-
CH 3
(2R,3S)-2,3 -epoxypentane
Source of chirality: Resolution by yeast epoxide hydrolase Absolute configuration: 2R,3S
A127
I Tetrahedron:Asymmetry 1997, 8, 639
C.A.G.M. Weijers
E.e. > 98% (by ehiml GC analysis) H
3
C5H1202
C
~
''''OH CH 3
(2R,3R)-2,3-pentanedioi
Source of chirality: Hydrolysis by yeast epoxide hydrolase Absolute configuration: 2R,3R
Tetrahedron: Asymmetry 1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai
D.e. > 99% (by chemical correlation) [0t]D20-- -89.3 (c 0.1, CHCI3) Source of chirality: (S,S)-1,3-diphenyl-1,3propanediol Absolute configuration 2"R,4"R, R (assigned by chemical correlation)
C35H2602 2",4"-diphenyl- l"5"-dioxa-2,2'-pentamethylene-1,1'-binaphthalene
Tetrahedron: Asymmetry 1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai B r P h ~ ' ~ , 7 . , ' P h Br
E.e.> 99% (by chemical correlation) [~]D20-- -26.3 (c 0.1, methanol) Source of chirality: (S,S)-1,3-diphenyl-1,3pmpanediol Absolute configuration 1R,3R (assigned by chemical correlation)
C35H26Br202 2',2"-bis(1-bromonaphthyl) 1,3-(1,3-diphenylpropyl)ether
I Tetrahedron:Asymmetry 1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai
D.e. > 99% (by HPLC analysis) [~]D20= +33.9 (c 0.1, CHCI3) Source of chirality: (2R,4R)-pentanediol Absolute configuration 2"S, 4"S, S (assigned by chemical correlation)
C25H2202 2",4"-dimethyl-l"5"-dioxa-2,2'-pentamethylene-1,l'-binaphthalene
A128
Tetrahedron:Asymmetry1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai Br
Br
C25H22Br202 2',2"-bis(l-bromonaphthyl) 2,4-pentyl ether
E.e.> 99% (by HPLC analysis) [Ct]D20=-21.8 (c 1.0, methanol) Source of chirality: (2R,4R)-pentanediol Absolute configuration 2S,4S (assigned by chemical correlation)
I Tetrahedron:Asymmetry1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai
D.e. > 99% (by HPLC analysis) [0t]D20= -308 (c 0.2, CHCI3) Source of chirality: (2R,4R)-pentanediol Absolute configuration 2"S, 4"S, R (assigned by chemical correlation)
C25H2202 2",4"-dimethyl- l"5"-dioxa-2,2'-pentamethylene-l,l'-binaphthalene
A129
Tetrahedron: Asymmetry 1997, 8, 497
J. T. Dougherty, J. R. Flisak. J. Hayes, I. Lantos, L. Liu* and L. Tucker
E.e. = 99% (by chiral HPLC using a CHIRALCEL-OD column) [O~]D 25 =
NO2
+19.9 (c = 1.0, DMF)
(S)-O-(2-nitrobenzyl)-N-(6-benzyloxy-2.3dihydrobenzofuran- 3-yl)-hydroxylamine
C22H~20~ Source of chirality: asymm, reduction Absolute configuration: 3S (assigned by correlation)
Nicolas Gautier, Nicolas Noiret*, Caroline Nugier-Chauvin and Henri Patin.
I
Tetrahedron:Asymmetry 1997, 8, 501
E.e.= 92% (;H-NMR)
ee
[O~]D20-- -3.71 (C 0.62, EtOH) Cell;sOS 1-butyl-3-butenyl sulphoxide
Source of chirality: the DAG methodology Absolute configuration: R
Tetrahedron: Asymmetry 1997,
R. C. Griesbach. D. P. G. Hamon and R. J. Kennedy,
8, 507
E.e.=98% [by NMR Eu(hfc) 3 shift experiments on the derived monoacetates]
OH
OH
Source of chirality: asymm, synth. (asymmetric dihydroxylation) Absolute configuration 2S confirmed by conversion to (S)-2(6-methoxy-2-naphthyl) propanoic acid
C14H1603 2-(6-methoxy-2-naphthyl)propan- 1,2-diol
I Tetrahedron:Asymmetry 1997,
R. C. Griesbach, D. P. G. Hamon and R. J. Kennedy,
8, 507
E.e.=98% [by NMR Eu(hfc)3 shift experiments on the derived monoacetates]
F
Source of chirality: asymm, synth. (asymmetric dihydroxylation)
OH
OH
Absolute configuration 2S confirmed by conversion to (S)-2(3-fluoro-4-phenylphenyl) propanoic acid
CI5H15FO2 2-( 3-fluoto-4-phenylphenyl)propan- 1,2-diol
A93
Tetrahedron:Asymmetry1997,8, 511
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal E.e. > 98°/.
O
~O ~
[Ot]D= -43.2 (c 1.0, CHCI3) Source of chirality:D(+)-Ribonic7-1actone
CO2Et
Absolute configuration:l R, 2R, 3R, 5S, 6S
C15H2oO5 (-)-(1 R, 2R, 3R, 5S, 6S)-Ethyl-2,3-cyclohexylidenedioxy-4-oxobicyclo[3,1,0]hexane-6-carboxylate
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
Tetrahedron:Asymmetry1997,8, 511
HN--CO
~ O
I OC/,,..NH
E.e. > 98% [(X]D= -107.2 (C 1.0, CHCI3)
~ C O 2 E t
Source of chirality:D(+)-Ribonic7-1actone Absolute configuration:l S, 2S, 3S, 4R, 5R, 6R
C17H22N203 (-)-(1 S, 2S, 3S, 4R, 5R, 6R)-Ethyl-3,4-cyclohexylidenedioxybicyclo[3,1,0]hexane-2-spiro-5'-hYdantoine-6carboxylate
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
~
I Tetrahedron:Asymmetry1997,8, 511
NCt,~NHCOCH3
E.e. > 98% [(X]D= -105.7 (cl.0, CHCI3)
o~~CO2
Source of chirality:D(+)-Ribonic7-1actone
Et
Absolute configuration: 1S, 2S, 3S, 4R, 5R, 6R
C1sH24N205 (-)-(1S, 2S, 3S, 4R, 5R, 6R)-Ethyl-2-acetamido-2-cyano-3,4--cyclohexylidenedioxybicyclo[3,1,0]hexane-6carboxylate
I Tetrahedron:Asymmetry1997,8, 51l
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal O
~CO2Et
E.e. > 98% [(z]D=-255 (cl .0, CH3OH) Source of chirality:D(+)-Ribonic7-1actone Absolute configuration:l R, 5S, 6S
C9H1003 (-)-(1 R, 5S, 6S)-Ethyl-4-oxobicyclo[3,1,0]-2-hexene-6-carboxylate
A94
I Tetrahedron:Asymmetry 1997, 8, 511
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
E.e. > 98%
0
[O[]D=+64.6 (C 1.0, CH3OH) Source of chirality:D(+)-Ribonic 7-1actone
~C02Et
Absolute configuration:l S, 5R, 6S
09H1203 (+)-(1 S, 5R, 6S)-Ethyl-2-oxobicyclo[3,1,0]-2-hexane-6-carboxylate
I Tetrahedron:Asymmetry 1997,8, 511
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal OC--NH I % HN,oo. =CO
E.e. > 98% [0~]D= -24 (C 0.5, MeOH)
~C02Et
Source of chirality:D(+)-Ribonic 7-1actone Absolute configuration:l S, 2S, 5R, 6S
C11H14N204 (-)-(1 S, 2S, 5R, 6S)-Ethyl bicyclo[3,1,0]hexane-2-spiro-5'-hydantoine°6-carboxylate
Tetrahedron: Asymmetry 1997,8, 511
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
E.e. > 98%
[e(]D=+74.0 (C 1.0, CHCI3)
O
H~o~CO2Et
Source of chirality:D(+)-Ribonic 7-1actone Absolute configuration:l S, 2R, 3R, 5S, 6S
C9H1205 (+)-(1 S, 2R, 3R, 5S, 6S)-Ethyl-2,3-dihydroxy-4-oxobicyclo[3,1,0]hexane-6-carboxylate
C. Domfnguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
O,
E.e. > 98%
O
HO ' = ~ , , , m
Tetrahedron: Asymmetry 1997,8, 511
[C£]D=-49.5 (c 0.4, CHCl3) CO2Et
Source of chimlity:D(+)-Ribonic 7-1actone
HO" Absolute configuration:IS, 3R, 4R, 5R, 6S CllH1606 (-)-(lS, 3R, 4R, 5R, 6S)-Ethyl-2,2-ethylenedioxy-3,4-dihydroxybicyclo[3,1,0]hexane-6-carboxylate
A95
Tetrahedron: Asymmetry 1997, 8, 511
C. Dom[nguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal E.e. > 98%
O,
[OC]D= -204.6 (cl .15, CHCI3)
O
Source of chirality:D(+)-Ribonic y-lactone
"~CO2Et
Absolute configuration: 1R, 5S, 6S CllH1404 (-)-(1 R, 5S, 6S)-Ethyl-4,4-ethylenedioxybicyclo[3,1,0]-2-hexene-6-carboxylate
Tetrahedron: Asymmetry 1997, 8, 511
C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal
E.e. > 98% [C~]D=+37.7 (C 0.65, HCI 1N)
H 2 N ~ , ~CO2H
Source of chirality:D(+)-Ribonic y-lactone Absolute configuration:IS, 2S, 5R, 6S C8H1104 (+)-(lS, 2S, 5R, 6S)-2-aminobicyclo[3,1,0]hexane-2,6-dicarboxylic acid
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
HOO)~
Cf
[~]~0 + 6.8 (c 0.56, H20) Source of chirality: (R)-prolinol Absolute configuration: R CTHj4CIN02
R-3-(2-Pyrrolidinyl)propanoic acid hydrochoride
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
[a]~° + 31.5 (c 0.7, CHCI3) Source of chirality: (R)-prolinol Absolute configuration: R C7HI INO (R)- l-Azabicyclo[3.3.0]octan-2-one
A96
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
[tx]~° 20.1 (c 1.49, CH3OH) Source of chirality: (R)-prolinol Absolute configuration: R C20H33NO8
EtOOC BOC EtOOC COOEr
(2R)-2-[2-(N-tert-Butoxycarbonylpyrrolidinyl)]- 1,1,1-tris-(ethoxycarbonyl)ethane
Tetrahedron: Asymmetry 1997, 8, 515
G.B. Giovenzana, M.Sisti and G. Palmisano
[t~]~° -26.3 (c 0.8, CHCI3) Source o f chirality: (R)-prolinol Absolute configuration: R C7HgNO
O
(R)- l-Azabicyclo[3.3.0]oct-3-en-2-one
Tetrahedron: Asymmetry 1997, 8, 519 David M. Hodgson and Robert E. Marriott
Ee = 35% (by chiral HPLC of 3,5-DNB deriv, of corresponding endo-alcohol) [a]D 20 = -18 (c 1.0, CHCI3) Source of Chirality: Desymmetrisation of achiral epoxide C9H 14°
using lithium (S,S)-bis(l-phenyl)ethylamide Absolute configuration (tentative): 1S,4S,5S,6R
endo-cis-5,6-Dimethylbicyclo[2.2. I ]heptan-2-one
(assigned by analogy to products observed with exo- and endo-norbornene oxides)
Tetrahedron: Asymmetry 1997, 8, 519 David M. Hodgson and Robert E. Marriott
Ee = 32% (by chiral HPLC of 3,5-DNB deriv, of corresponding endo-alcohol) [a]D 2° = +8 (c 0.5. CHCI3) Source of Chirality: Desymmetrisation of achiral epoxide C7HtoO
using lithium (S,S)-bis( l-phenyl)ethylamide Absolute configuration: IS,4R
Bicyclo[2.2. I ]heptan-2-one
(assigned by comparison of sign of [aid of ketone with lit.)
A97
I Tetrahedron:Asymmetry 1997,
David M. Hodgson and Robert E. Marriott
8, 519
Opticalpurity= 19% [O~]D20 = -99 (c 0.5, CHCI3) Source of Chirality: Desymmetrisation of achiral epoxide using lithium (S,S)-bis(I-phenyl)ethylamide
CsHioO
Absolute configuration: IS,4S Bicyclo[2.2.2]oct-5-en-2-one
(assigned by comparison of sign of [or]o of ketone with lit.)
I Tetrahedron:Asymmetry 1997,
J. A. Hyatt and Chad Skelton
TBDMS-O~
8, 523
E.e. = > 95% (chiral column HPLC) mp = 60-65 ° [C~]24 D : + 14.7 (C = 0.42, CHCI3) Absolute configuration: 2S Source of chirality: Enzyme-catalysed kinetic resolution
cH°
Tetrahedron: Asymmetry 1997, 8, 523
J. A. Hyatt and Chad Skelton
0
HO~o CH20~CO2H
E.e.=96.5% (chiral-column HPLC) mp 97-100 ° [ot]24o= +0.48 (0.50, CHCI3) Absolute configuration 2S Source of chirality: Enzyme-catalysed kinetic resolution
(S)-6-Hydroxy-2,5,7,8-tetramethyl-2chromanmethanol succinate
Tetrahedron: Asymmetry 1997,
J. Meiwes, M. Schudok, G. Kretzschmar
BrH2~NCOzH
E.e. > 9 9 . 8 % ( O P A derivatization and I-IPLC) [oq20 = -29.3 ( c = l , H 2 0 ) Source ofehirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C7HsBrNO2S L-3-(4-bromo-2-thienyl)alanine
A98
8, 527
Tetrahedron: Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
Cl'laH2~CO2 H
E.e. >99.8% (OPA derivatization and HPLC) [t~]20 = -19.6 (c=l, H20 ) Source ofchirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C8H1 INO2 S L-3-(5-methyl-2-thienyl)alanine
I Tetrahedron:Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
CO2H NH2
E.e. >99.8% (OPA derivatization and HPLC) [OQ2D 0 =-38.9 (c=l, n20) Source of chirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C7H9NO2S L-3-(3-thienyl)alanine
Tetrahedron: Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
H2~CO2 H
E.e. >99.8% (OPA derivatization and HPLC) [=1~° = - 3 0 . 3 ( c = l , H20) Source ofchirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C7H9NO2S L-3-(2-thienyl)alanine
Tetrahedron: Asymmetry 1997, 8, 527
J. Meiwes, M. Schudok, G. Kretzschmar
CHs
E.e. >99.8% (OPA derivatization and HPLC) [t~]20 = -8.8 (c=l, 1N NaOH)
H2~N~ CO2H
Source ofchirality: chemo-microbial asymmetric synthesis Absolute configuration: 2S
C8H11NO2S L-3-(3-methyl-2-thienyl)alanine
A99
M. Smr~ina,* S. Vysko~il, J. Polfvkovti, J. Pol~kov~, J. Sejbal, V. Hanu§, M. Pol,~§ek, H. Verrier, and P. Ko(~ovsk3/*
I
I
Tetrahedron: Asymmetry 1997, 8, 537
E.e. 97% [by chiral HPLC] mp 158-160 °C (EtOH or petroleum ether-CH2CI2) OCSNMe2 [a]o -154 (c 0.1, CHCI3) or -111 (c 1.0, THF) [ ~ OCSNMe2 Source of chirality: (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl (BINOL) Absolute configuration: S 026H24N202S2 (assigned by genetic relation to BINOL) 2,2'-Di[(N,N-dimethylthiocarbamoyl)oxy]-1,1'-binaphthyl
M. Smr(Sina,*S. Vysk06il, J. Polfvkowl, J. Poh~kov~i,J. Sejbal, V. Hanu.~,M. Pol~i.~ek,H. Verrier, and P. Ko6ovsk3/*
I
I
Tetrahedron: Asymmetry 1997, 8, 537
E.e. >99% [by chiral HPLC] mp 183-184 °C (MeOH) OCSNMe2 [~(]D-144 (C 0.5, CHCI3) [ ~ SCONMe2 Source of chirality: (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl (BINOL) Absolute configuration: S 026H24N202S2 (assigned by genetic relation to BINOL) 2-[(N,N-dimethylthiocarbamoyl)oxy]-2'-[(N,N-dimethylcarbamoyl)mercapto]-1,1'-binaphthyl
M. Smn~ina,* S. Vysko~il, J. Polfvkov~,J. Pola.kov~,J. Sejbal, V. Hanu§, M. Pol~i.~ek,H. Verrier, and P. Ko~ovsk3/*
SH
020H140S 2-Hydroxy-2'-mercapto-1,1 '-binaphthyl
E.e. > 98% [by 1H NMR of the derivative with (-)-menthyl chloroformate] [a]D +5.7 (c 0.9, EtOH) Source of chirality: (S)-(-)-2,2'-dihydroxy-1,1'-binaphthyl (BINOL) Absolute configuration: S (assigned by genetic relation to BINOL)
M. Smr~ina,* S. Vysko6il, J. Polfvkov~,J. Pol~ikov~i,J. Sejbal, V. Hanu~, M. Pol~i~ek,H. Verrier, and P. Ko~ovsk~;*
~
NHCOCH 3 OH
022H17NO2 2-(Acetamido)-2'-hydroxy-1,1'-binaphthyl
Tetrahedron: Asymmetry 1997, 8, 537
Tetrahedron: Asymmetry 1997, 8, 537
E.e. >99% [by chiral HPLC] mp 208-208.5 °C (EtOH) [Ct]D-79 (C 0.5, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydmxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
A100
Tetrahedron: Asymmetry 1997, 8, 537
v
M. Smrcina,* S. Vysko~il, J. Polfvkov~i,J. Pol~kov~, J. Sejbal, V. Hanu§, M. Polfi.~ek,H. Verrier, and P. Ko~ovs~ *
~
NHCOCH 3 OCOCH3
024H19NO3 2-(Acetamido)-2'-acetoxy-1,1'-binaphthyl
mp 162-163 °C (MeOH) [cx]o-88 (c 1, CHCla) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
I
Tetrahedron: Asymmetry 1997, 8, 537 M. Smr~ina,* S. Vyskot~il,J. Polfvkov~,J. Polfikovfi, J. Sejbal, I V. Hanu~,, M. Pol~.~ek, H. Verrier, and P. Ko~ovsk~ * [ ~ E.e. >99% [by chiral HPLC] mp 66-68 °C (n-heptane) NHCOCH3 [aiD -20 (C 0.5, CHCI3) OCSNMe2 Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S 02sH22N202S (assigned by genetic relation to NOBIN) 2-(Acetamido)-2'-[(N,N-dimethylthiocarbamoyl)oxy]-1,1'-binaphthyl
M. Smrdina,* S. Vysko~il, J. Polfvkov~,J. Polfikovfi, J. Sejbal, V. Hanu.~,M. Pol~.~ek,H. Verrier, and P. Ko~ovsk~ *
~
NHCOCH3 SCONMe2
I
I
Tetrahedron: Asymmetry 1997,
8, 537
E.e. >99% [by chiral HPLC] [~]D -190 (C 0.5, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
C25H22N202S 2-(Acetamido)-2'-[(N,N-dimethylcarbamoyl)mercapto]-I,1'-binaphthyl
I Tetrahedron:Asymmetry 1997, 8, 537 M. Smr~ina,* ,~. Vysko~U,J. Poffvkovd.,J. Pol~kov~, J. Sejbal, V. Hanu~,, M. Pol~§ek, H. Verrier, and P. Ko~ovsk~ * E.e. >97.4% [by chiral HPLC of its hydrobromide] mp 127-131 °C (dec; EtOH) NH2 [tZ]o +19 (c 0.1, CHCI3) SH Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN) C2oH15NS 2-Amino-2'-mercapto-1,1'-binaphthyl
~
AIOI
Tetrahedron: Asymmetry 1997,
8, 537
M. Smr~ina,* S. Vysko~il, J. Polrvkov~,J. Pol~kov~, J. Sejbal, V. Hanu.~,M. Pol~§ek, H. Varrier, and P. Ko~ovslo~* [ ~ E.e. >99% [by chiral HPLC] mp 194-194.5 °C (toluene) NMe2 [a]D -32.6 (C 1, THF) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN) C22H19NO 2-(N,N-Dimethylamino)-2'-hydroxy-1,1'-binaphthyl
@°"
Tetrahedron: Asymmetry 1997, 8, 537 M. Smr~ina,* ,S. Vysko6il, J. Polrvkov~[,J. Poi~kowl, J. Sejbal, V. Hanu§, M. Pol~§ek, H. Verrier, and P. Ko~ovsk9 * E.e. 98.2% [by chiral HPLC] [ ~ mp 120-122 °C (CH2CI2-heptane) NMe2 [ct]D -8.8 (c 1, THF) OCSNMe2 Source of chiral~y: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S C25H24N2OS (assigned by genetic relation to NOBIN) 2-(N,N-Dimethylamino)-2'-[(N,N-dimethylthiocarbamoyl)oxy]-1,1'-binaphthyl
Tetrahedron: Asymmetry 1997,
M. Smr~ina,* ,~. Vysko6il, J. Polrvkovd,J. Pol~.kov~,J. Sejbal, V. Hanu.~,M. Pol~§ek, H. Verrier, and P. Ko~ovslo~*
~
NMe2
SCONMe2
8, 537
[Ct]D-25 (C 0.4, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
025H24N2OS 2-(N,N-Dimethylamino)-2'-[(N,N-dimethylcarbamoyl)mercapto]-1,1'-binaphthyl
I
"Asymmetry 1997,
8, 537
M. Smr~ina, S. Vysko~il, J. Polrvkovd,J. Pol~kov~i,J. Sejbal, V. Hanu§, M. Pol,~§ek,H. Verriar, and P. Ko~ovsk~ * E.e. 96.2% [by chiral HPLC] mp 124-126 °C (toluene-petroleumether 1:1) NMe2 [a]O -27 (C 0.4, THF) SH Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1'-binaphthyl (NOBINI Absolute configuration: S (assigned by genetic relation to NOBIN) C22H19NS 2-(N,N-Dimethylamino)-2'-mercapto-1,1'-binaphthyl
~
A102
M. Smr~ina,* S. Vysko~il, J. Polfvkov~, J. Pol~kov~;, J. Sejbal, V. Hanu.~, M. Pol~ek, H. Verrier, and P. Ko~.ovs~ *
~
NMe
Tetrahedron: Asymmetry 1997, 8, 537
E.e. 52.8% [by ehiral HPLC] [cold+114 (c 0.4, CHCI3) Source of chirality: (S)-(-)-2-amino-2'-hydroxy-1,1 '-binaphthyl (NOBIN) Absolute configuration: S (assigned by genetic relation to NOBIN)
C22H15NOs
Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Novak and L. Poppe HO~OAc O-~- O
I
I
CsH 1~,O5 3-hydroxy-2-acetoxymethylpropanal dimethyl acetal
E.e.= 44% [~H-NMR of MTPA ester] 12(} a]~ = +4.1 (c=l, acetone) Source ofchirality: enzymatic acetylation Absolute configuration: R (assumed by analogy with the other members of the series)
Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Novak and L. Poppe H O ~ O_A c
J
O1"~O
L.
E.e.= 71% [tH-NMR of MTPA ester ] [oriel'= +4.9 (c=l, acetone) Source of chirality: enzymatic acetylation
C BoH2oO5 3-hydroxy-2-acetoxymethylpropanal diethyl acetal
Absolute configuration: R (determined by chemical transformation into a compound with known absolute configuration)
I Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Novb.k and L. Poppe HO.-"~f,'~OAc
E.e.= 68% [IH-NMR of MTPA ester] [ot]t~i'=+3.7 (c=l, acetone) Source ofchirality: enzymatic acetylation
CI6H3205 3-hydroxy-2-acetoxymethylpropanal di-i-amylacetal
Absolute configuration: R (assumed by analogy with the other members of the series)
A103
Tetrahedron: Asymmetry 1997, 8, 547
G. Egri, E. Fogassy, L. Nov~ik and L. Poppe HO.,."',,,z,,,"~ OA c
E.e.= 70% [IH-NMR of MTPA ester] [ot]l:i)=+7.4 (c=l, acetone)
O.J'-,O
Source ofchirality: enzymatic acetylation
C20H2405 3-hydroxy-2-acetoxymethylpropanal dibenzylacetal
Absolute configuration: R (assumed by analogy with the other members of the series)
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o -.o
I Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(~]D22= +35 (C = 2.0 in CHC13)
~OCPh3
Source of chirality: synthesis from natural product
C)H C2sH2sO4
Absolute configuration: 2R, 4S, 5R
2-Methyl-4-(trityloxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
J--o L~-~.OC
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
H2Ph
OH C~3H1804
[(~.]D22 = -----0.5(C = 3.9 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
2-Methyl-4-(benzyloxymet~yl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o.J-.o
L~OSitBuPh2 0
C221-t2804Si
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
[CI-]D22= - - 5 1 (c = 4.6 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S
2-Methyl-4-(t-butyldiphenylsilyloxymethyl)1,3-dioxan-5-one
A104
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o
~
E.e.
OCPh3
O 025H2404 2-Methyl-4-(b'ityloxymethyl)1,3-dioxan-5-one
=
[0~]D22
100% (by preparation method) =
----49.5 (c = 3.6 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o
L~CX~I-12Ph 0
C13H1BO4
Tetrahedron: Asymmetry 1997, 8, 559
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct.]D22 = --36 (c = 3.8 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S
2-Methyl-4-(benzyloxymethyl)1,3-dioxan-5.-one
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/1-.o L~ositBuPh2 0 022H2sO4Si 2-Methyl-4-(t-Ixltyldiphenylsilyloxymethyl)1,3-dioxan-5-one
E.e. = 100% (by preparation method) [0/,]D22 = +82 (c = 1.0 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o L~OCPh3 0 Czs~404
Tetrahedron: Asymmetry 1997, 8, 559
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [C[,]D22 = +51 (c = 2.6 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R
2-Methyl-4-(trityloxymethyl)1,3-dioxan-5-one
A105
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-.o L,~OCI..12 Ph 0 013H1604 2-Methyl-4-(benzyloxymethyl)1,3-dioxan-5-one
E.e. = 100% (by preparation method) [Ct]D22= +57 (C = 2.0 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R
M. Carda, P. Casab6, F. Gonz~ilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/1..o %L~oSitBuPh2 ~%OH C23H3204Si
Tetrahedron: Asymmetry 1997, 8, 559
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(X]D22 =
+14 (c = 3.5 in CHCI3)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
2,5-Dimet~yl--4-(t-butyldiphenylsilyloxyme~yl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonz~ilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(X]D22 =
+5.4 (C = 1.1 in CHC6)
Source of chirality: synthesis from natural product C7H1404
Absolute configuration: 2R, 4S, 5R
2,5-Dimethyl-4-(hydroxymet~yl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I-.o %L~OCI-~Ph %"OH C141-12oO4
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Gt,]D22 =
+20.5 (c = 1.8 in CHC13)
Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
2,5-Dirnethyl-4-(benzyloxymethyl)1,3-dioxan-5.-ol
A106
M. Carda, P. Casab6, F. Gonz~ez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/i--o ~'OH C2e~804 2,5-Dimethyl-4-(trityloxyrnethyl)1,3-dioxan-5-ol
E.e. = 100% (by preparation method) [ot]t)z2= +4.7 (c = 5.1 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4S, 5R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and JA. Marco. OH J'~ A /OCH2Ph HO" ~"OH v
Tetrahedron: Asymmetry 1997, 8, 559
I Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [0£]D22 = ---8.2 (c = 1.5 in CHCI3)
Source of chirality: synthesis from natural product C12HlsO4 4-O-Benzyl-2-rnethylbutane-1,2,3,4-te'o'aol
Absolute configuration: 2R, 3S
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A Marco. .OCH2Ph ~ /OCH2Ph PhCH20" /%"OH v
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D22= +10.2 (C = 6.0 in CHCI3) Source of chirality: synthesis from natural product
C261-1~O4 1,3.4-Tri-O-benzyl-2-meth~bul~lne-1,2,3,4-tetraol
Absolute configuration: 2R, 3S
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o 1.. o
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
_ ..L~ ~OSitBuph2
[G£]D22 = - - 5 . 6 (c = 2.5 in CHCI3)
"'/%OH
Source of chirality: synthesis from natural product
C241"13404Si
Absolute configuration: 2R, 4S, 5R
5-Ethyl-2-methyl-4-(t-butyldiphenylsilyloxymethyl)1,3-dioxan-5-ol
AI07
M. Carda, P. Casab6, F. Gonz/dez, S. Rodriguez, L.R. Domingo and J.A. Marco.
Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [a]o22 = - - 1 3 . 0 (c = 5.6 in CHC13) Source ofchirality: synthesis from natural product Absolute configuration: 21L 4S, 5R
CaHlsO4 5-Ethyl-2-methyl-4-(hydroxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/1-.o ~% ~
I Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
OCH2ph
[ct]o22 =--2.1 (c = 1.4 in CHCI3)
Source of chirality:synthesisfrom naturalproduct ClsH2204
Absolute configuration:2R, 4S, 5R
5-Ethyl-2-rnet~yl-4-(benzyloxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonz/dez, S. Rodriguez, L.R. Domingo and J.A. Marco.
o/I--o ~"~'OH C27H3004
I Tetrahedron:Asymmetry 1997, &
559
E.e. = 100% (by preparation method) [ct]022 =----3.6 (c = 5.5 in CHC13) Source of chirality: synthesis from natural product Absolute configuration: 21L 4S, 5R
5-Ethyl-2-methyl-4-(tdtyloxyrnethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco. Old
Tetrahedron:Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D22= --11.5 (C = 0.34 in CHCh) Source of chirality: synthesis from natural product
C13H2004 4-O-Benzyl-2-ethylbutane-1,2,3,4-tetTaol
Absolute configuration: 2R, 3S
AI08
M. Carda, P. Casab6, F. Gonz~ez, S. Roddguez, L.R. Domingo and J.A. Marco.
~ p hCI.-~O . ~ , , O H
.OCI.-12Ph /OCI'I2Ph Y
Tetrahedron:Asymmetry1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D22= +9.0 (C = 2.6 in CHCI3) Source of chirality: synthesis from natural product
C2d-13~4 1,3.4-Tri-O-benzyl-2-ethylbutane-1,2,3,4-teU'aol
Absolute configuration: 2R, 3S
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-~
Tetrahedron:Asymmetry1997, 8, 559
Ee. = 100% (by preparation method) OSitBuPh2
[C¢.]D22= +8.8 (c = 5.5 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
C23H3204Si 2,5-Dimethyl..4-(t-butyldiphenylsilyloxymethyl)1,3-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzalez, S. Rodriguez, L.R. Domingo and JA. Marco.
oJ-._o
I Tetrahedron:Asymmetry1997, 8, 559
E.e. = 100% (by preparation method) [ct]022 = +17.0 (c = 0.8 in CHC13) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
C7H1304 2,5-Dimethyl-4-(hydroxymethyl)1,3.-dioxan-5-ol
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-. ~
I Tetrahedron:Asymmetry1997, 8, 559
E.e. = 100% (by preparation method) OCH2Ph
C14H~O4
[ff,]D 22 =
+15.5 (c = 1.6 in CHC13)
Source ofchirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
2,5-Dime~yi-4-(benzyloxymethyl)1,3.-dioxan-5.-ol
A109
M. Carda, P. Casab6, F. Gorghlez, S. Rodriguez, L.R. Domingo and JA. Marco.
1.o ~
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) OCPh3
/'"OH
026H2804 2,5-Dimethyl-4-(ttityloxymethyl)1,3-dioxan-5-ol
[Ct]D22= +5.5 (C = 1.9 in CHCI3) Source of chirality: synthesis from natural product Absolute configuration: 2R, 4R, 5R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco. QH
/~...~ /OCH2Ph HO" ~"OH v
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [a]D 22= +6.4 (C = 1.1 in CHC13) Source of chirality: synthesis from natural product
C12H1804 4-O-Benzyl-2-me~ytbutane-1,2.3.4-tetraol
Absolute configuration: 2R, 3R
Tetrahedron: Asymmetry 1997, 8, 559 M. Carda, P. Casab6, F. Gonzalez, S. Rodfiguez, L.R. Domingo and J.A. Marco. ()CH2Ph A /OCH2Ph PhCH20" / " O H /~.
E.e. = 100% (by preparation method) [Ct]D22 = --2.6 (C = 0.4 in CHC13) Source of chirality: synthesis from natural product
c2d-~04 1,3.4-Tri-O-benzyl-2-methylbutane-1,2,3,4-tetraol
Absolute configuration: 2R, 3R
M. Carda, P. Casab6, F. Gonz~ilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
¢-o
_ ~O6itBuPh2
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D 22 =
+14.5 (c = 4.0 in CHCi3)
Source of chirality: synthesis from natural product C24H3404Si 5-Ethyi-2-met~yi-A-(t-butyldiphemylsilyloxyrnethyl)1,3-dioxan-5-ol
Absolute configuration: 2R, 4R, 5R
All0
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, L.R. Domingo and J.A. Marco.
J-o
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [Ct]D:2= +17.5 (C = 0.7 in CHCI3) Source of chirality: synthesis from natural product
C8H1604 5-Ethyl-2-methyl-4-(hydroxymethyl)1,3-dioxan-5-.d
Absolute configuration: 2R, 4R, 5R
M. Carda, P. Casab6, F. Gonzhlez, S. Rodriguez, L.R. Domingo and J.A. Marco.
oJ-.o
E.e. = 100% (by preparation method)
_ ~OCH2Ph "~'~"
Tetrahedron: Asymmetry 1997, 8, 559
[(X]D22 =
+18.5 (c = 1.6 in CHCI3)
Source of chirality: synthesis from natural product
" "OH
Absolute configuration: 2R, 41L 5R
ClsPe204 5-E~yl-2-methyl..4-(l~n zylo~o/n'~thyl)1,34ioxan-5-~l
M. Carda, P. Casab6, F. Gonzhlez, S. Rodfiguez, L.R. Domingo and JA. Marco.
oJ-.
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method) [(g]D22 = +5.0 (c = 28 in CHCIs)
~'OH
Source of chirality: synthesis from natural product
C27H~04 5-E~yl-2-methyl-4-(tm'yloxymethyl)1,3-dioxan-5-ol
Absolute configuration: 2R, 4R, 5R
M. Carda, P. Casab6, F. Gonzfilez, S. Rodriguez, UR. Domingo and J.A. Marco. ~H
H O ~
Tetrahedron: Asymmetry 1997, 8, 559
E.e. = 100% (by preparation method)
OCH2Ph
[(X]D22 =
+6.5 (c = 1.5 in CHCI3)
Source of chirality: synthesis from natural product C1a~oO4
4-O-Benzyt-2-ethylbutane-1,2,3,4-tetraol
Absolute configuration: 2R, 3R
Alll
Tetrahedron:Asymmetry 1997, 8, 559
M. Carda, P. Casab6, F. Gonzfi/ez, S. Rodriguez, L.R. Domingo and J.A. Marco.
OCH2Ph P h C H 2 0 ~ OCH2Ph
E.e. = 100% (by preparation method) [CqD22= - - 9 . 3 (C = 0.1 in CHCh) Source of chirality: synthesis from natural product
C27He204
Absolute configuration: 2R, 3R
1,3.4-Td-O-benzyl-2-ethylbutane-1,2,3,4-tetraol
I
F. Dumas*, K. Aiencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa*
OH
"Asymmetry 1997,
8, 579
ee > 92 % [~]D 20= -51.9 (c = 1.9, EtOHabs) Source of chirality: (1S)-(-)-13-pinene (92 % ee) Absolute configuration: IR, 2R, 3S, 5R
CI6H220 3-Benzyl nopinol
l Tetrahedron:Asymmetry 1997,
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa*
OH MeO~~"~ C 17H24O 3-[(4-Methoxyphenyl)-methyl] nopinol
8, 579
ee > 92 % Mp 47 °C (pentane) [~]D20 = -25.3 (c = 1.74, EtOHab s) Source of chirality: (IS)-(-)-13-pinene (92 % ee) Absolute configuration: 1R, 2R, 3S, 5R
I Tetrahedron:Asymmetry 1997,
F. Dumas a*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconceilos*, P.R.R. Costa*
ee > 92 % [0£]020 = -30.9 (c = 2.1, EtOHab s) Source of chirality: (1S)-(-)-B-pinene (92 % ee) Absolute configuration: 1R, 2R, 3S, 5R C 17H24O
3-[(2-Methoxyphenyl)-methyl] nopinol i
All2
8, 579
J Tetrahedron:Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa*
ee > 92 % Mp 112 °C (pentane) [O~]D20 = -54.0 (c = 1.45, EtOHabs) Source of chirality: (1S)-(-)-13-pinene (92 % ee) Absolute configuration: IR, 2R, 3S, 5R
C20H240 3-[( 1-Naphthyl)-methyl] nopinol
J Tetrahedron:Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa* OH
ee > 92 % [(/.]D20 = -11.4 (c = 1.8, EtOHabs) Source of chirality: (lS)-(-)-8-pinene (92 % ee) Absolute configuration: 1R, 2R, 3S, 5R
C20H24O 3-[(2-Naphthyl)-methyl] nopinol
Tetrahedron: Asymmetry 1997, 8, 579 F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa* OH
C 16H22O 3-Benzyl nopinol
ee > 92 % Mp 110 °C (Et20:pentane 1:1) [O~]D20 ---- -42 (c = 2, EtOHabs) Source of chirality: (IS)-(-)-13-pinene (92 % ee) Absolute configuration: 1R, 2S, 3S, 5R
Tetrahedron: Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. G6rard, M.L. Vasconcellos*, P.R.R. Costa* OH
C17H24O
3-[(4-Methoxyphenyl)-methyl] nopinol
ee > 92 % Mp 112 °C (pentane) [0~]D20 = -51.6 (C = 1.4, EtOHa~) Source of chirality: (IS)-(-)-B-pinene (92 % ee) Absolute configuration: 1R, 2S, 3S, 5R
All3
Tetrahedron: Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. GErard, M.L. Vasconcellos*, P.R.R. Costa* OMe
ee > 92 % [ct]o2° = -57.3 (c = 1.5, EtOHabs) Source of chirality: (1S)-(-)-B-pinene (92 % ee) Absolute configuration: IR, 2S, 3S, 5R
OH
C17H240 3-[(2-Methoxyphenyl)-methyl] nopinol
Tetrahedron: Asymmetry 1997, 8, 579
F. Dumas*, K. Alencar, J. Mahuteau, M. J. Barbero C. Miet, F. GErard, M.L. Vasconcellos*, P.R.R. Costa* O
+
ee = 92 % [ot]D2° = + 17.6 (neat) Source of chirality: (1S)-(-)-f3-pinene (92 % ee) Absolute configuration: IS, 5S
C9H 14° Nopinone
Tetrahedron: Asymmetry 1997, 8, 591
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard Ph
ee " 85% (by chiral HPLC analysis) [Ot]D =-91.9 (c 1%, MeOH-HCI) CIsHI7NO (R)-(-)- l-(4-methoxyphenyl)-2-phenylethylamine
Tetrahedron: Asymmetry 1997, 8, 591
P. Moreau, M. Essiz, J.Y. MErour and D. Bouzard
H2S© Ph
ee ' 94% (by chiral HPLC analysis) [Ct]D =-118 (c 1.01%, MeOH-HCI) [OqD = -10.1 (c 1.34%, CHCI3)
CI4H15N R-(-)- 1,2-diphenylethylamine
All4
Tetrahedron:Asymmetry1997,8, 591
P. Moreau, M. Essiz, J.Y. M6rour and D. Bouzard.
ee : 88% (by chiral HPLC analysis) [~]D =-4.4 (c 1.02%, MeOH-HCI) C18H17N (R)-(-)- 1-(1)-naphtyl-2-phenylethylamine
l Tetrahedron:Asymmetry1997, 8, 591
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard Ph
ee: 77% (by HPLC chiral analysis) [Ct]D =-117 (c 1.02%, MeOH-HCI) C 14I-I14CIN (R)-(-)- l-(4-chlorophenyl)-2-phenylethylamine
I Tetrahedron:Asymmetry1997,
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard
8, 591
Ph ee : 84% (by chiral HPLC analysis) [~t]D =-95 (c 1.01%, MeOH-HC1)
c ~20N2 (R)-(-)- l-(4-dimethylaminophenyl)-2-phenylethylamine
I Tetrahedron:Asymmetry1997, 8, 591
P. Moreau, M. Essiz, J.Y. Merour and D. Bouzard.
ee : 75% (by chiral HPLC analysis) cto = -43.5 ° (c 1%, MeOH-HCI) ee > 99% (by chiral HPLC analysis) [Ct]D = -94 (c 1.01%, MeOH-HCI) C21H21NO (R)-(-)- 1-(2-benzyloxyphenyl)-2-phenylethylamine
All5
Tetrahedron: Asymmetry 1997, 8, 599
ValmtinaFAVERO,OimniI~RZI E ! S¢~gioSANDRI
[a] ~= -297.7 (c= 2.5, chloroform)
Source of chirality : (S)-phenylethylamine Absolute configuration : 6R, I'S assigned by 1H-NMR C13H16N202
(6R, l'S)-l-(l'-Phenethyl)-6-methyl-piperazine-2,5-dione
I
ValmlimFAVERO, GianniPORZIand SmgioSANDRI
: Asymmetry 1997, 8, 599
[a]~= 37.8 (c= 2.13, chloroform) IJ Source of chirality: (S)-phenylethylamine Absoluteconfiguration: 6S,I'S assignedby IH-NMR C13H16N202
(6S,1 'S)- 1-( 1'-Phenethyl)-6-methyl-piperazine-2,5-dione
Tetrahedron: Asymmetry 1997, 8, 599
ValenfinaFAVERO,GianniPORZIsad SergioSANDRI )C2Hs
CH~ [a]~= -288.4 ( ~ 2.71, chloroform) L,P Source of chirality : (S)-phenylethylamine Absolute configuration : 6R, I'S assigned by 1H-NMR C15I-I20N202
CH 3 0
(6R, l'S)-l-(l'-Phenethyl)-5-ethoxy-6-methyl-3,6-dihydro-lH-pyrazine-2-one
I Tetrahedron:Asymmetry 1997, 8, 599
ValentinaFAVERO.GiaaniPORZIand SergioSANDRI
{I)C2H$ [a]~= 37.5 ( ~ 2.1, chloroform) Source of chirality : (S)-pimnylethylamir~ Absolute configuration : 6s, r s assigned by 1H-NMR CI5H20N202
(6S,l'S)-l-(l'-Phenethyl)-5-ethoxy-6-methyl-3,6-dihydro-lH-pyrazine-2-one
All6
I Tetrahedron:Asymmetry1997, 8, 599
Vakalina FAVERO,GialmiPORZIand Sa'gio SANDRI
tit
I-Is
[a,]~= -5.1 ( ~ 8.4, chloroform) S o u ~ of chirality : (S)-pbcnylethylamin¢ Absolute configuration : 31L6S,1'S assigned by 1H-NMR C20H28N202
CH3 0
(3•L6S•••S)••-(•••phenethy•)•5-eth•xy•3-(3•methy•-2•buteny•)-6-methy••3•6-dihydr•-•H-pyrazine•2••ne
Tetrahedron:Asymmetry1997, 8, 599
ValentinaFAVERO,Gianni PORZI and SczgioSANDRI
|
II CH~
CH3
[¢z]~=-16 (c= 4.8, chloroform) Sou~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H-NMR C20H28N202
O
(3S,6S, 1•S)-•-(•'-Phenethy•)-5-eth•xy-3-(3-methy•-2-buteny•)-6-methy•-3•6-dihydr•-•H-pyrazine-2-•ne
I Tetrahedron:Asymmetry1997, 8, 599
ValentinaFAVERO,Gianni PORZI and SergioSANDRI
C2Hs phCH~
CH3
[¢x]_25=40.3 (c= 2.2, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR C18H26N202
CH3 0 (3R,6S,1 'S)- 1-( 1'-Phenethyl)-5-ethoxy-3-isopropyl-6-methyl-3,6-dihydro- 1H-pyrazine-2-one
I Tetrahedron:Asymmetry1997, 8, 599
ValmfinaFAVERO,Gianni PORZI and Sergio SANDRI
C2Hs
[a]~= 17.1 ( ~ 3.7, chloroform) S o u ~ of ehirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by IH-NMR C18H~N202
3 (3R,~,l'S)-l-(l'-~yl)-5-etl~]-3-allyl-~me.Ihyl-3,f~tglydm-!H-p~2~
All7
Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIandSel'gioSANDRI
[~]~-- -14.3 (c= 0.5, chloroform) D Source of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H-NMR C18H24N202 3
(3S•6S•••S)•••(•'•Phenethy•)-5-eth•xy-3•a••y•-6-methy•-3•6-dihydr•-•H•pyrazine-2-•ne ValentinaFAVERO,GianniPORZIand~ )C2Hs
Ph
, N!," ~ .31/
Ph
Tetrahedron: Asymmetry 1997, 8, 599
SANDRI
[a]_25= -209.1 (c= 3.1, chloroform) Source of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C22H26N202
(35,6R, l'S)- 1-(l'-Phene~yl)-5--e~oxy-3-benzyl-6-me~yl-3,6-dihydm-1H-pyrazine-2-one I Tetrahedron:Asymmetry 1997, 8, 599
ValeatlnaFAVERO,GianniPORZIand SergioSANDRI
~C~Hs
[ix]_25=-237 (e= 1.9, chloroform) D Source of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR
Ph~cHN ~ ' ~ C H 3
CI8H26N202
3
(3S,6R, 1'S)- 1-( 1'-Phenethyl)-5-ethoxy-3 -propyl-6-methyl-3,6-dihydro-1H-pyrazine-2-one Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIandSergioSANDRI
p
N
CH3
[0t]25= -256 (e= 1.4, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C16I-I22N202
(3S,6R, l'S)-l-(l'-l:~nethyl)-5--ethoxy-3,6-dime~yl-3,6--dihydro- 1H-pyrazine-2-one
All8
Tetrahedron: Asymmetry 1997, 8, 599
ValeatinaFAVERO,GiaaniPORZIand Se~gioSANDRI )C2Hs
[¢x]p= -132.8 (c= 2.4, chloroform) S o u ~ of ehirality : (S)-phenylethylamine Absolute configuration : 3R,6R, I'S assigned by 1H-NMR CIsH24N202
CH 3 0
(3R,6R, I'S)- 1-(l'-Phenethyl)-5-ethoxy-3-allyl-6-methyl-3,6-dihydro-lH-pyrazine-2-one I Tetrahedron:Asymmetry 1997, 8, 599
ValeatinaFAVERO,GianniPORZ]and SergioSANDRI C2Hs
CH~ ~ . p h . ~ , N , ~
3
[a]25= -248.5 ( ~ 6.8, chloroform) Sou~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C]TH24N202
CH3 0 (3S•6R••'S)-•-(•'-Phenethy•)-5-eth•xy-3-ethy•-6-methy•-3•6-dihydr•-•H-pyrazine-2-•ne Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIand SergioSANDRI C2Hs
CH~.,
N
Ph-~N',~",f
CH3
[a]25= -132.6 (c= 1.8, chloroform) Sou°reeof chirality : (S)-phenylethylamine Absolute configuration : 3R,6R,I'S assigned by 1H-NMR CtTH24N202
CH 3 O
(3R,6R,I'S)- 1-(l'-Phenethyl)-5-ethoxy-3-ethyl-6-methyl-3,6-dihydro-lH-pyrazine-2-one Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO.GianniIK)RZIand SexgioSANDRI
~ C2Hs
cH3~, .,.~.
[a] 25=-211.2 (c= 11.4,chloroform) Source of chirality : (S)-phenylethylamine Absoluteconfiguration: 3S,6R, I'S assignedby IH-NMR C20H28N202
(3S,6R,l'S)-l-(l'-Phenethyl)-5-ethoxy-3-(3-methyl-2-butenyl)-6-methyl-3,6-dihydro1H-pyrazine-2-one
All9
Val~_0~ FAVERO,
I Tetrahedron:Asymmetry 1997,8, 599
Giarmi~3R2~ end SergioSANDRI
)C2H$ [(X]~= -268.4 (effi2.1, chloroform) S o ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR
ClsH26N202 (3S,6R,1~3)-1-(l'-Phenethyl)-5-ethoxy-3-isopropyl-6-methyl-3,6-dihydro-1H-pyr~zine-2-one
Al~sa~aMADAU,~ CH~.~.
Tetrahedron: Asymmetry 1997,8, 599
PORZIand S~o S/dDRI
IHs
[ct]~=-264.1 (c= 1.7, chloroform) Sou~r.e of chirality : (S)-phenylethylamine Absolute configuration : 3S,6R,1'S assigned by 1H-NMR C18HuN202
(35,6R,1'S)- 1-(l'-Phene~yl)-5-ethoxy-3-allyl-6-me~yl-3,6-dihydm- 1H-pyrazine-2-one Tetrahedron: Asymmetry 1997,8, 599
ValentinaFAVERO,GianniPORZIandSergioSANDRI
•C2Hs
C
p
, N
CH3
[~]25= 18.2 (c= 0.9, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR
CI6H22N202
(3R,6S, l'S)-l-(l'-l:~ene~yl)-5--ethoxy-3,6-dime~yl-3,6-d~ydm- ltt-pyrR~ne-2-one ValesuinaFAVERO, GianniIK)RZl and
C2Hs
CIt,N ~
I Tetrahedron:Asymmetry 1997,8, 599
SergioSANDRI
[~]~= -20.3 (e= 2.2, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H-NMR CI6H22N202
(3S,6S,l'S)-l-(l'-P~ae~yl)-5-ethoxy-3,6-dime~yl-3,6-dihydm-lH-p~-2..one
AI20
V ~
FAVERO, Oiaam PORZI sml S ~
I Tetrahedron:Asymmetry1997, 8, 599
SANDRI
[Ct]~= -184.7 (c= 3.7, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3R,6R,1'S assigned by 1H-NMR p
, N
s
CH3
CI6I-I~N202
(3R,6R, I'S)- 1-(l'-Pl~ne~yl)-5-e~oxy-3,6-dime~yl-3,6-dihydm- 1H-pyrazine-2-one
I Tetrahedron:Asymmetry1997, 8, 599
ValeatinaFAVERO, OiamniFORZI and S~rgioSANDRI
C2Hs
[a]~= 156.8 (e= 1.5, chloroform) Source of chirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR
C22H~'~202 (3R,6S,l'S)-l-(l'-Phone~yl)-5-ethoxy-3-benzyl-6-methyl-3,6-dihydm- 1H-py~ziqe-2-one
VsdealinaFAVERO,~ C2Hs
I Tetrahedron:Asymmetry1997, 8, 599
PORZIand SetgioSANDRI
[tz]~= 19.6 (e= 0.4, chloroform) Source of ehirality : (S)-phenylethylamine Absolute configuration : 3R,6S,1'S assigned by 1H-NMR
CmH~',1202 CH 3 0
(3R,6S, 1'S)- 1-( 1'-Phenethyl)- 5-ethoxy-3 -propyl-6-methyl- 3,6-dihydro- 1H-pyrazine-2-one
Tetrahedron:Asymmetry1997, 8, 599
ValeatiaaFAVERO, GianniPORZI aad Seqio SANDRI
[a]~= -20.8 (c= 1, chloroform) S o u ~ of chirality : (S)-phenylethylamine Absolute configuration : 3S,6S,1'S assigned by 1H.NMR
CmH~I202 CHa O (3S,6S,1 'S)- 1-( 1'-Phenethyl)- 5-ethoxy-3-propyl-6-methyl-3,6-dihydro- 1H-pyrazine-2 -one
AI21
Tetrahedron: Asymmetry 1997, 8, 599
ValentinaFAVERO, Oi~nl PO~Zl and Se~io SANDRI
? C21ts
cH,,,...,k.
CH3
[oq~= -32 (c= 2.8, chloroform) D Source of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R assigned by 1H-NMR CI2H20N202
(3S,6R)-5-ethoxy-3-(3-methyl-2-butenyl)-6-methyl-3,6-dihydro-lH-pyrazine-2-one Tetrahedron: Asymmetry 1997, 8, 599
ValenfinaFAVERO,GianniPORZIand SergioSANDRI
~ C2H5
CH~, I~.
[cx]_25=23.3 (c= 2.4, chloroform) S o u ~ of ehirality : (S)-phenylethylamine Absolute configuration : 3S,6R assigned by 1H-NMR C14HIsN202
0
(3S,6R)-5-ethoxy-3-benzyl-6-methyl-3,6-dihydro-lH-pyrazine-2-one I Tetrahedron:Asymmetry 1997, 8, 599
ValentinaFAVERO,GianniPORZIand SergioSANDRI CH3 ,,, / C O O C 2 H s ' " ( C H 22C H =. C (~C H 3 )
H/N'~" NH3+CI"
[oq25= 28.9 (c= 3.1, chloroform) Sot~ce of chirality : (S)-phenylethylamine Absolute configuration : 2R,5S assigned by 1H-NMR C12H23C1N203
(2R,5S)-2-methyl-5-amino-3-aza-4-oxo-8-methyl ethyl-7-nonenoate hydrochloride Tetrahedron: Asymmetry 1997, 8, 599
Valentina FAVERO, Giaani PORZI and Sergio SANDRI
CH3,,,~/COOC2Hs "f ~HlPh HtN~NHCOCH3
[(x]25= -7 (c = 1.07, chloroform) LI Source of chirality : (S)-phenylethylamine Absolute configuration : 2R,5S assigned by 1H-NMR C16H22N204
(2R,5S)-2-methyl-5-acetamido-3-aza-4-oxo-6-phenyl ethyl-hexanoate
A122
ValeatinaFAVERO,Gianai~)RZIandSefgioSAN'DR/
Tetrahedron: Asymmetry 1997,
8, 599
[o.]_~= 37.1 ( ~ 2.9, chloroform) Sott~ee of ehirality : (S)-ethyl lactate Absolute configuration : 6R assigned by 1H.NMR
CH3N ~ N I H
CI2HI4N202 (6R)-1 -N-Benzyl-6-rnethyl-piperazine-2,5 -dione
ValenlinaFAVERO,GianniPORZIandSetgioSANDRI
I Tetrahedron:Asymmetry 1997, 8, 599
[or]25= -22.5 (c= 2.9, chloroform) D Source of chirality : (S)-ethyl lactate Absolute configuration : 6R assigned by 1H-NMR
CH3~,...~N H5
C14H18N202
Ph
0
(6R)-l-N-Benzyl-5-ethoxy-6-methyl-3,6-dihydro- 1H-pyrazine-2-one
I Tetrahedron:Asymmetry 1997, 8, 619
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
CH2\ / COOCH2OH3 /C. OH 2
NH 2
(+)-(S)-2',1': 1,2;l",2":3,4-Dinaphthcyclohepta-l,3-diene-6-amino-6-carboxylic acid ethyl ester. C26H23NO 2. [0~]25589 = +316.6, [(~]25578 = +331.1, [ec]25546 = +376.8, [0~]25436 = +603.3, [0~]25365 = +306.2 (c 0.5; MeOH).
Tetrahedron: Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
CH2
NH 2
(+)-(S)-2', 1': 1,2; 1" , 2 " :3,4-Dinaphthcyclohepta- 1,3-diene-6-amino-6-carboxylic acid tertbutyl ester. C28H27NO2. [(z]25589 = +309.8, [(x]25578 = +324.0, [(z]25546 = +368.4, [e~]25436 = +590.4 (c 0.5; MeOH).
A123
8, 619
Tetrahedron: Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~)avrdaand M. Wakselman
~
8, 619
O-12\ /COOH CH~"C~NH2
(+)-(S)-2', 1 ': 1,2; 1",2":3 ,4-Dinaphthcyclohepta- 1,3-diene-6-amino-6-carboxylic acid. C24HI9NO2. [~]25589 = +314.3, [~]25578 = +327.9, [5]25546 = +375.0, [a] 25436 = +616.7, [~]25365 = +423.3 (c 0.6; MeOH).
Tetrahedron: Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~)avrdaand M. Wakselman
8, 6 t 9
C. c C°°C.2C.3 CH2
NHCOOC(CH3) 3
(+)-(S)-2', 1': 1,2;1",2" 3,4-Dinaphthcyciohepta- l 3-diene-6-tert-buty]oxycarbonylan~no-6carboxytic acid ethyl ester. C31H31NO4. [o{]25589 = +38.5, [oc]25578 = +39.3, [c~]25546 = +41.0, [0~]25436 = -0.1, [0~]25365 = -599.7 (C 0.6; MeOH).
I Tetrahedron:Asymmetry 1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
8, 619
CH2\ /COOC(CH3)3 jC\ OH2 N H(X~,(CH3 )3
(+)-(S)-2', 1' : 1,2; 1 " , 2 " :3,4-Dinaphthcyclohepta- 1,3-diene-6-tert-butyloxycarbonylarmno-6carboxylic acid tert-butyl ester. C33H35NO4. [o~]25589 = +38.7, [(z]25578 = +39.0, [0t]25546 = 25 4-41.0, [0[] 436 = -2.8, [~]25365 = -601.5 (c 0.5; MeOH).
Tetrahedron: Asymmetry 1997, 8, 619
J.-P. Mazaleyrat, * A. Gaucher, J. ~)avrdaand M. Wakselman
CH2
NH(XX)(~aC0H s
(+)-(S)-2', 1': 1,2; 1",2' ' :3,4-Dinaphthcyclohepta- 1,3-diene-6-benzyloxycarbonylamino-6carboxylic acid tert-butyl ester. C36H33NO4. [ct]25589 = +10.0, [1~]25578 = +9.5, [~]25546 = +6.6, [ff,]25436 -- -63.5, [o{]25365 = -684.4 (c 0.5; MeOH).
A124
I Tetrahedron:Asymmetry1997,
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
CH2\ /CO(~ CH27C'NHCOOC(CH3)3
(+)-(S)-2', 1': 1,2; 1" ,2" :3,4-Dinaphthcyclohepta- 1,3-diene-6-tert-butyloxycarbonylanfino-6carboxylic acid. C29H27NO4. [t~]2%89 = +46.6, [ct]25578 = +47.6, [~]25546 = +50.2, [Ct]25436 +8.6, [1~]25365 = -644.6 (C 0.5; MeOH).
=
I[ Tetrahedron:Asymmetry1997, 8, 6 i 9
J.-P. Mazaleyrat, * A. Gaucher, J. ~avrda and M. Wakselman
~
8, 619
Ct-12\ /1200t-I C H ~ C\NHCOOCH2C6H5
(+)-(S)-2', 1': 1,2; 1" ,2" :3,4-Dinaphthcyclohepta- 1,3-diene-6-benzyloxycarbonylamino-6carboxylic acid. C32H25NO4. [ct]25589 = +15.1, [~]25578 = +14.9, [(~]25546 = +12.9, [~]25 436 = 25 -56.0, [Ct] 365 = - 7 1 2 . 0 (c 0.5; MeOH).
I Tetrahedron:Asymmetry1997,
B. B. Lohmy * and S. Venkateawarlu
O
8, 633
= > 81% (determined based on optical rotation) [CqD21 = -31.5 (c, 0.5, CHCI3)
ee
~C10H21 i OAc
Source of chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 5R0 6S
(5R, 6 S)-6-Acetoxy-5-hexadecanolide
Tetrahedron:Asymmetry1997,
B. B. Lohray * and S. Venkatemwarlu
OMe
o
ee = 81% (determined based on optical rotation of final product) laiD 21 = -28.8 (c, 3.34, CHCI3) Source of chirality : Asymmetric dihydroxylation of corresponding olefin
ClcH21
Absolute configuration : 4S, 5S
(48, 5S)-4-Carbomethoxybutyl-5-decyl-l,3,2-dioxathiolane-2,2-dioxide
A125
8, 633
Tetrahedron:Asymmetry1997,
B. B. Lohmy * and S. Venlmteswarlu
8, 633
= c a . 8 1 % (determined based on optical rotation of final product) [aiD 21 = - 10.1 (C, 1.0, CHCI3)
ee
OM@
Source o! chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 5S, 6S
C~cH21 Methyl (5S, 6S)-5,6-dihydroxyhexadecanoate
I Tetrahedron:Asymmetry 1997, 8, 633
B. B. Lohray * and S. Venkateewadu
OMe
ee = ca. 8 1 % (determined based on optical rotation of final product) [(X]D21 = - 42.3 (C,1.0, CHCI3)
/(3
Source of chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 4S, 5S
CloH21
(4S, 5S )-Carbomethoxybutyl-5-decyl-1,3,2-dioxathiolane-2-oxide
I Tetrahedron:Asymmetry 1997, 8, 633 B. B. Lohray * and S. Venkateewarlu
O
~ C l o H 2 1 = OH (5R, 6 S)-6-hydroxy-5-hexadecanolide
ee = > 8 1 % (determined based on optical rotation) [aiD 21 = -12.5 (c, 0.54, CHCI3) Source of chirality : Asymmetric dihydroxylation of corresponding olefin Absolute configuration : 5R, 6S
Tetrahedron:Asymmetry1997,
C.A.G.M. Weijers
E.e. > 98% (by GC analysis with a-Cyclodextrin column)
Source of chirality: Resolution by yeast epoxide hydrolase C9HI00
Absolute configuration: 1 R,2R
(1R,2R)-1-Phenyl- 1,2-epoxypropane
A126
8, 639
I
C.A.G.M. Weijers
H
Tetrahedron:Asymmetry 1997, 8, 639
OH E.e. > 98% (by GC analysis with 13-Cyelodextrin column) CH 3 [Ct]D24= - 32.8 (C = 0.6, CHC13) Source of chirality: Hydrolysis by yeast epoxide hydrolase
C9H 1202 (1R,2S)- l-Phenyl- 1,2-propanediol
Absolute configuration: 1 R,2S
I Tetrahedron: Asymmetry 1997, 8, 639
C.A.G.M. Weijers
E.e. > 98% (by GC analysis with ~t-Cyclodextrin column)
Source of chirality: Resolution by yeast epoxide hydrolase Absolute configuration: 1S,2R,4S C10HI60 (1S,2R,4S)-1,2-Epoxy-8-p-menthene
Tetrahedron: Asymmetry 1997, 8, 639
C.A.G.M. Weijers
~--
.... ,OH
E.e. > 98% (by GC analysis with 13-Cyclodextrin column)
Source of chirality: Hydrolysis by yeast epoxide hydrolase Absolute configuration: 1R,2R,4S C1oH1802 (1R,2R,4S)-8-p-Menthene- 1,2-diol
Tetrahedron: Asymmetry 1997, 8, 639
C.A.G.M. Weijers ,11IO
H3C
CsH10 O
'
E.e. > 98% (by chiral GC analysis)
-:-
CH 3
(2R,3S)-2,3 -epoxypentane
Source of chirality: Resolution by yeast epoxide hydrolase Absolute configuration: 2R,3S
A127
I Tetrahedron:Asymmetry 1997, 8, 639
C.A.G.M. Weijers
E.e. > 98% (by ehiml GC analysis) H
3
C5H1202
C
~
''''OH CH 3
(2R,3R)-2,3-pentanedioi
Source of chirality: Hydrolysis by yeast epoxide hydrolase Absolute configuration: 2R,3R
Tetrahedron: Asymmetry 1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai
D.e. > 99% (by chemical correlation) [0t]D20-- -89.3 (c 0.1, CHCI3) Source of chirality: (S,S)-1,3-diphenyl-1,3propanediol Absolute configuration 2"R,4"R, R (assigned by chemical correlation)
C35H2602 2",4"-diphenyl- l"5"-dioxa-2,2'-pentamethylene-1,1'-binaphthalene
Tetrahedron: Asymmetry 1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai B r P h ~ ' ~ , 7 . , ' P h Br
E.e.> 99% (by chemical correlation) [~]D20-- -26.3 (c 0.1, methanol) Source of chirality: (S,S)-1,3-diphenyl-1,3pmpanediol Absolute configuration 1R,3R (assigned by chemical correlation)
C35H26Br202 2',2"-bis(1-bromonaphthyl) 1,3-(1,3-diphenylpropyl)ether
I Tetrahedron:Asymmetry 1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai
D.e. > 99% (by HPLC analysis) [~]D20= +33.9 (c 0.1, CHCI3) Source of chirality: (2R,4R)-pentanediol Absolute configuration 2"S, 4"S, S (assigned by chemical correlation)
C25H2202 2",4"-dimethyl-l"5"-dioxa-2,2'-pentamethylene-1,l'-binaphthalene
A128
Tetrahedron:Asymmetry1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai Br
Br
C25H22Br202 2',2"-bis(l-bromonaphthyl) 2,4-pentyl ether
E.e.> 99% (by HPLC analysis) [Ct]D20=-21.8 (c 1.0, methanol) Source of chirality: (2R,4R)-pentanediol Absolute configuration 2S,4S (assigned by chemical correlation)
I Tetrahedron:Asymmetry1997, 8, 649
T. Sugimura, H. Yamada, S. Inoue and A. Tai
D.e. > 99% (by HPLC analysis) [0t]D20= -308 (c 0.2, CHCI3) Source of chirality: (2R,4R)-pentanediol Absolute configuration 2"S, 4"S, R (assigned by chemical correlation)
C25H2202 2",4"-dimethyl- l"5"-dioxa-2,2'-pentamethylene-l,l'-binaphthalene
A129