Palladium-catalyzed [3+2] annulation of N-sulfinylanilines with vinylethylene carbonates and vinyl epoxides has been reported, affording the 1,2,3-oxathiazolidine-2-oxides under mild reaction conditions. Further synthetic applications of 1,2,3-oxathiazolidine-2-oxides in the preparation of sulfoxides, β-amino alcohols and amines have also been demonstrated.

Abstract

A palladium-catalyzed [3+2] annulation reaction of N-sulfinylanilines with vinylethylene carbonates and vinyl epoxides is developed. It affords 1,2,3-oxathiazolidine-2-oxides under mild reaction conditions through allylic palladium intermediates. The versatile synthetic utility of 1,2,3-oxathiazolidine-2-oxides in preparing sulfoxides, β-amino alcohols, and substituted amines has also been demonstrated.