Photoredox/Enzymatic Catalysis Enabling Redox-Neutral Decarboxylative Asymmetric C–C Coupling for Asymmetric Synthesis of Chiral 1,2-Amino Alcohols
Yiyin Liu, Liangyan Zhu, Xuemei Li, Yunfeng Cui, Atefeh Roosta, Jinhui Feng, Xi Chen, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
Abstract
High Resolution Image Download MS PowerPoint Slide Photocatalysis offers tremendous opportunities for enzymes to access new functions. Herein, we described a redox-neutral photocatalysis/enzymatic catalysis system for the asymmetric synthesis of chiral 1,2-amino alcohols via decarboxylative radical C–C coupling of N -arylglycines and aldehydes by combining an organic photocatalyst, eosin Y, and carbonyl reductase RasADH. Notably, this protocol avoids using any sacrificial reductants. A possible reaction mechanism proposed is that the transformation proceeds through sequential photoinduced decarboxylative radical addition to an aldehyde and a photoenzymatic deracemization pathway. This redox-neutral photoredox/enzymatic strategy is promising not only for effective synthesis of a series of chiral amino alcohols in a green and sustainable manner but also for the design of other novel C–C radical coupling transformations for the synthesis of bioactive molecules.