Asymmetric synthesis of protected α-hydroxyaldehydes via reduction of α-arylthio-β-oxosulphoxides

Abstract

The complex metal hydride reduction of α-arylthio-β-oxosulphoxides to the corresponding alcohols is highly stereospecific. The stereochemical course of the reaction has been determined and a detailed examination of the factors responsible for the stereospecificity has been made. The asymmetric reduction has been used to synthesise protected α-hydroxyaldehydes in high optical purity starting from (+)-(S)-p-tolyl p-tolylthiomethyl sulphoxide and acyl chlorides.