STEREOSELECTIVE SYNTHESIS OF F-ALKYL ALPHA,BETA-UNSATURATED ESTERS AND THEIR EPOXIDATION

Authors
LANIER M HADDACH M PASTOR R RIESS JG
Citation
M. Lanier et al., STEREOSELECTIVE SYNTHESIS OF F-ALKYL ALPHA,BETA-UNSATURATED ESTERS AND THEIR EPOXIDATION, Tetrahedron letters, 34(15), 1993, pp. 2469-2472
Citations number
32
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
15
Year of publication
1993
Pages
2469 - 2472
Database
ISI
SICI code
0040-4039(1993)34:15<2469:SSOFAE>2.0.ZU;2-H
Abstract
Strong electrophilic Z and E 3-F-alkyl 2-propenoates have been prepare d stereoselectively. Their extremely difficult epoxidation has been ac hieved with retention of stereochemistry using t-BuO2Li, leading to F- alkyl glycidic esters, which are useful building blocks for the synthe sis of new amphiphiles.