Remarkably Mild and Simple Preparation of Sulfenate Anions from β-Sulfinylesters: A New Route to Enantioenriched Sulfoxides

Abstract

[reaction: see text] A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using beta-sulfinylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulfenates are subsequently converted into sulfoxides in good to excellent yield. Extension of the methodology to an unprecedented access to nonracemic sulfoxides by introduction of an enantiopure ligand, (-)-sparteine, is also described.