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

doi:10.1021/jacsau.3c00366

Photoredox/Enzymatic Catalysis Enabling Redox-Neutral Decarboxylative Asymmetric C-C Coupling for Asymmetric Synthesis of Chiral 1,2-Amino Alcohols

JACS Au. 2023 Oct 31;3(11):3005-3013. doi: 10.1021/jacsau.3c00366. eCollection 2023 Nov 27.

Authors

Yiyin Liu^{1

2}, Liangyan Zhu^{1

2}, Xuemei Li^{1

2}, Yunfeng Cui^{1

2}, Atefeh Roosta^{1

2}, Jinhui Feng^{1

2}, Xi Chen^{1

2}, Peiyuan Yao^{1

2}, Qiaqing Wu^{1

2}, Dunming Zhu^{1

2}

Affiliations

¹ National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China.
² National Technology Innovation Center for Synthetic Biology, Tianjin 300308, China.

Abstract

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.