Enantioselective Alkyl C−H Sulfimidation Enabled by Copper Catalysis

Enantioselective transformation of alkanes into functional chiral molecules constitutes an ultimate goal for chemists that however, has been a grand challenge over more than half century. Although remarkable advances have been made in the stereoselective C-C, C-N and C-O bonds formation enabled by either metal or enzyme catalysis, the alkyl C-H sulfimidation for building up a stereogenic sulfur center from alkanes has not previously been accomplished. Herein, we describe a photoinduced copper-catalyzed enantioselective C−H sulfimidation of alkanes, allowing for a straightforward synthesis of highly enantioenriched sulfilimines from alkane feedstocks. Computational studies and mechanistic investigations unveil the reaction mechanism and the origin of stereoselectivity.