1. Asymmetric Paired Electrolysis: Enantioselective Alkylation of Sulfonylimines via C(sp3)−H Functionalization.
- Author
-
Tao, Yongsheng, Ma, Wan, Sun, Rui, Huang, Cheng, and Lu, Qingquan
- Abstract
Enantioselective transformation of ubiquitous C(sp3)−H bonds into three‐dimensional chiral scaffolds is of longstanding interest to synthetic chemists. Herein, an asymmetric paired electrolysis enables a highly efficient and sustainable approach to the enantioselective alkylation of sulfonylimines via C(sp3)−H functionalization. In this protocol, anodic oxidation for benzylic radical formation and Lewis acid‐catalyzed sulfonylimine reduction on the cathode were seamlessly cross‐coupled (up to 88 % yield). Enantioenriched chiral amines containing a tetrasubstituted carbon stereocenter are accessed with high enantioselectivity (up to 96 % ee). Mechanistic studies suggest that the amine generated in situ could serve as a base to deprotonate phenols and decrease the oxidation potential of the reaction, allowing phenols with lower potentials to be preferentially oxidized. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF