STEREOCONTROLLED SYNTHESIS OF ALPHA-TRIALKYLSILYL-BETA,GAMMA-UNSATURATED ALDEHYDES VIA PALLADIUM(0) CATALYSIS - SYNTHETIC USEFULNESS

Authors
LEBIDEAU F GILLOIR F NILSSON Y AUBERT C MALACRIA M
Citation
F. Lebideau et al., STEREOCONTROLLED SYNTHESIS OF ALPHA-TRIALKYLSILYL-BETA,GAMMA-UNSATURATED ALDEHYDES VIA PALLADIUM(0) CATALYSIS - SYNTHETIC USEFULNESS, Tetrahedron, 52(21), 1996, pp. 7487-7510
Citations number
60
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
21
Year of publication
1996
Pages
7487 - 7510
Database
ISI
SICI code
0040-4020(1996)52:21<7487:SSOA>2.0.ZU;2-1
Abstract
The reaction of silicon substituted vinyloxiranes in the presence of c atalytic amount of palladium (0) catalyst affords the title compounds. This new reaction proceeds smoothly, under very mild conditions and w ith complete chirality transfer. One-pot addition of selected organome tallic nucleophiles to these aldehydes at very low temperature led to a highly selective preparation of the corresponding alcohols in very g ood yields. Influence of substituents on the silicon atom and of the l igands of palladium have been studied. Copyright (C) 1996 Elsevier Sci ence Ltd