Desymmetrization–Addition Reaction of Cyclopropenes to Imines via Synergistic Photoredox and Cobalt Catalysis

作者：Xiang‐Kui He, Liang‐Qiu Lu, Bao‐Ru Yuan, Jia-Long Luo, Ying Cheng, Wen‐Jing Xiao · 发表于：Journal of the American Chemical Society · 年份：2024 · DOI：10.1021/jacs.4c07096 · 被引用次数：53 · 研究领域：Cyclopropane Reaction Mechanisms、Catalytic C–H Functionalization Methods、Radical Photochemical Reactions

Herein, we designed a reaction for the desymmetrization-addition of cyclopropenes to imines by leveraging the synergy between photoredox and asymmetric cobalt catalysis. This protocol facilitated the synthesis of a series of chiral functionalized cyclopropanes with high yield, enantioselectivity, and diastereoselectivity (44 examples, up to 93% yield and >99% ee). A possible reaction mechanism involving cyclopropene desymmetrization by Co-H species and imine addition by Co-alkyl species was proposed. This study provides a novel route to important chiral cyclopropanes and extends the frontier of asymmetric metallaphotoredox catalysis.