Stereocontrolled synthesis of alpha-trialkylsilyl-beta,gamma-unsaturated aldehydes via palladium(0) catalysis. Synthetic usefulness

The reaction of silicon substituted vinyloxiranes in the presence of catalytic amount of palladium (0) catalyst affords the title compounds. This new reaction proceeds smoothly, under very mild conditions and with complete chirality transfer. One-pot addition of selected organometallic nucleophiles to these aldehydes at very low temperature led to a highly selective preparation of the corresponding alcohols in very good yields. Influence of substituents on the silicon atom and of the ligands of palladium have been studied. Copyright (C) 1996 Elsevier Science Ltd