The asymmetric synthesis of allylic alcohols using a recoverable chiral sulphoxide

Abstract The enantiomerically pure cyclic sulphinamide S (S) R-(+)- 3 reacts with the sodium enolates of ketones to give the corresponding homochiral sulphoxides. Reduction of the carbonyl group in these products using DIBAL-H or DIBAL-H/ZnBr 2 gives complementary products of high diastereoisomeric excess. This methodology has been applied to the synthesis of an allylic alcohols in high enantiomeric excess.