Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization
Siyuan Tang, Zhan-Jie Wang, Ao Yu, Ning Wang, Huan‐Ming Huang
Abstract
Asymmetric multicomponent reactions that aim to control multiple chiral centers with high selectivity in a single step remain an on-gonging challenge. The realm of enantioselective radical-polar crossover transformation achieved through C-H Functionalization has yet to be fully explored. Herein, we present a successful description of a photoredox/Cr-catalyzed enantioselective three-component (hetero)arylalkylation of 1,3-dienes through C-H functionalization. A diverse array of chiral homoallylic alcohols could be obtained in good to excellent yields, accompanied by outstanding enantioselectivity. The asymmetric radical-polar crossover transformation could build two chiral centers simultaneously and demonstrates broad substrate tolerance, accommodating various drug-derived aldehydes, (hetero)aromatics, and 1,3-diene derivatives. Preliminary mechanistic studies indicate the involvement of a radical intermediate, with the chiral allylic chromium species reacting with various aliphatic and aromatic aldehydes through Zimmerman–Traxler transition states enabled by dual photoredox and chiral chromium catalysis. Asymmetric multicomponent reactions that aim to control multiple chiral centers with high selectivity in a single step remain an ongoing challenge. Here, the authors present a photoredox- and chromium-catalyzed enantioselective three-component (hetero)arylalkylation of 1,3-dienes through C-H functionalization.