Highly Stereoselective Vinylogous Pummerer Reaction Mediated by Me₃SiX

Abstract

A highly stereoselective vinylogous Pummerer rearrangement involving 1,4-migration of the sulfinyl oxygen atom occurs when ortho-sulfinyl benzyl carbanions are treated with trimethylsilyl halides. The reaction proceeds in good yield and affords optically pure benzyl alcohols with extremely high enantioselectivity (ee > 98%).