Simultaneous Construction of Sulfur and Carbon Stereocenters via Asymmetric Desymmetrization of Sulfonimidamides With Oxindole Derivatives

Abstract

ABSTRACT Sulfonimidamides are highly appealing owing to their capacity for extensive structural diversification and their broad‐spectrum, versatile bioactivities. In the present work, functionalized chiral sulfonimidamides bearing both 1,3‐ S (VI)‐ and C ‐stereocenters were successfully synthesized via the desymmetrization of sulfonimidamides, which was realized by the highly diastereo‐ and enantioselective conjugate addition of 3‐bromo‐3‐substituted oxindoles to sulfonimidamides, with a chiral N,N ′‐dioxide/Ni(II) complex serving as the Lewis acid catalyst. This transformation features mild reaction conditions, excellent functional group tolerance, and a broad substrate scope.