Synthesis of Chiral Sulfonimidoyl Chloride via Desymmetrizing Enantioselective Hydrolysis
Gao-feng Yang, Yi Yuan, Tian Yin, Shiqi Zhang, Xin Cui, Bing Xia, Guangxun Li, Zhuo Tang
Abstract
Direct construction of chiral S(VI) from prochiral S(II) is a formidable challenge due to the inevitable formation of stable chiral S(IV). Previous synthetic strategies rely on the conversion of chiral S(IV) or enantioselective desymmetrization of preformed symmetrical S(VI) substrates. Here, we report desymmetrizing enantioselective hydrolysis of in situ-generated symmetric aza-dichlorosulfonium from sulfenamides for the preparation of chiral sulfonimidoyl chlorides, which could be used as a general stable synthon for obtaining a series of chiral S(VI) derivatives.
Topics & Concepts
Enantioselective synthesisDesymmetrizationChemistrySynthonHydrolysisOrganic chemistryChlorideCombinatorial chemistryStereochemistryCatalysisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques