Diastereoselective Access to anti-β-Hydroxy Sulfoxides from ­Chiral Epoxides and Prochiral Sulfenate Anions: Mechanistic ­Insights, Scope, and Limitation

Abstract

AbstractReported herein is a stereoselective route to anti-β-hydroxy sulfoxides through the reaction of epoxides with sulfenate anions. Extensive experimental/computational studies revealed the dual special roles of MgBr2·OEt2, serving to generate the bromohydrin alkoxide intermediate, which undergoes nucleophilic attack on the prochiral sulfenate in a diastereoselective manner. The present study has opened a general stereoselective synthetic route to anti-β-hydroxy sulfoxides.