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

Reported 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. [ABSTRACT FROM AUTHOR]