Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O -silylated cinnamyl alcohols

Abstract

A very fast [1,4] carbon-to-oxygen silicon migration-rearrangement leading to O-silylated cinnamyl alcohols occurs when the carbanion generated from sulfone 1 is reacted with carbonyl compounds. The mandatory role of the adjacent phenyl ring in this process is demonstrated when compared to the behaviour of the corresponding unsubstituted sulfone 3.