Complementary Strategy for Regioselective Synthesis of Diverse β‐Hydroxysulfones from Thiosulfonates

Abstract

The regioselective synthesis of variously substituted β‐hydroxysulfones from thiosulfonates was developed. The reactions of thiosulfonates and alkenes via a peroxy radical intermediate provided 2° and 3° β‐hydroxysulfones in good yields. The presence of epoxides instead of alkenes changed the reaction mechanism to nucleophilic addition involving sulfinate anions to afford 1° and 2° β‐hydroxysulfones. By using both protocols, the regiochemical outcome of the β‐hydroxysulfones synthesized from thiosulfonates was diversified.