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

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.