HIGHLY EFFICIENT AND STEREOSELECTIVE ACCESS TO (Z)-ALPHA,BETA-DIFLUOROALLYL ALCOHOLS AND (Z)-ALPHA-FLUORO-ALPHA,BETA-UNSATURATED ALDEHYDES BASED ON THE REACTION OF 2,3,3-TRIFLUORO-1-PROPENYL P-CHLOROBENZENESULFONATE WITH GRIGNARD-REAGENTS

Authors
FUNABIKI K FUKUSHIMA Y INAGAKI T MURATA E MATSUI M SHIBATA K
Citation
K. Funabiki et al., HIGHLY EFFICIENT AND STEREOSELECTIVE ACCESS TO (Z)-ALPHA,BETA-DIFLUOROALLYL ALCOHOLS AND (Z)-ALPHA-FLUORO-ALPHA,BETA-UNSATURATED ALDEHYDES BASED ON THE REACTION OF 2,3,3-TRIFLUORO-1-PROPENYL P-CHLOROBENZENESULFONATE WITH GRIGNARD-REAGENTS, Tetrahedron letters, 39(14), 1998, pp. 1913-1916
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
14
Year of publication
1998
Pages
1913 - 1916
Database
ISI
SICI code
0040-4039(1998)39:14<1913:HEASAT>2.0.ZU;2-2
Abstract
2,3,3-Trifluoro-1-propenyl p-chlorobenzenesulfonate (1), readily avail able from 2,2,3,3-tetrafluoropropanol, reacted smoothly with various G rignard reagents at 50 degrees C to afford the corresponding (Z)-alpha ,beta-difluoroallyl alcohols 2 in moderate to excellent yields. These alcohols were smoothly hydrolyzed in the presence of a catalytic amoun t of mentmorillonite K10 (Clay) to provide (Z)-alpha-fluoro-alpha,beta -unsaturated aldehydes 3 in good yields. (C) 1998 Elsevier Science Ltd . All rights reserved.