Novel synthesis of perfluoroalkyl epoxy esters

144

Al6 Novel synthesis of perfluoroalkyl

epoxy

esters

M. Lanier, M. Haddach, R. Pastor and J. G. Riess de Chimie Moticul.aire, URA 426, Universitb de Nice-Sophin Sciences, 06108 Nice Cedex 2 (France)

Laboratoire FacultS ok

Antipolis,

Polyfunctional F-alkylated intermediates such as polyols, aminoalcohols and aminoacids are needed for the synthesis of new F-alkylated compounds. In the hydrocarbon series, epoxides are generally used as precursors of such intermediates, but their perfluoroalkylated analogues are difhcult to prepare. We report here new methods for preparing 3-F-alkyl-2,3-epoxypropanoates stereoselectively: a Ph2P=CH

CO@

RFCOCl

c

pH2

R$rCC02Et

Pd/CaCO@‘d

bA

RFHco2Et H

z

:%$:I

H

t

R$OOH

,,!,,t

w

CH 3C02Et

Rz+fo2Et

*%

/ NaH p

i RFCOCH2C02Et

lgO2Et

NaBH4 / AC. Ta w -20%

RFHCO2Et H

R$H(OH)CH2C02Et

OH

+ R$H(OH)CH2@H)

_ _ _ --_ kL

RF CH(OH) dH OH

Ring-opening of the new F-alkylated epoxides by nucleophilic should provide many opportunities for further work.

agents