REACTION OF ENOLATES OF ACYLTRIMETHYLSILANES WITH ALDEHYDES. CANNIZZARO TYPE OXIDATION-REDUCTION REACTION WITH A TRIMETHYLSILYLCARBONYL GROUP

Article abstract of DOI:10.1246/cl.1980.525

The reaction of an acyltrimethylsilane enolate with 2 eq of an aldehyde gives a 1:2 adduct, while that with the enolate of an α-chloroacyltrimethylsilane affords an α,β-unsaturated aldehyde as a 1:1 adduct accompanied by the carboxylic acid derived from the starting aldehyde.An oxidation-reduction reaction mechanism on the trimethylsilylcarbonyl group has been proposed.