Work

Enantioselective Synthesis of Chiral γ‐Amino Acid Esters via Photoredox/Nickel‐Catalyzed Aryl‐Aminoalkylation of Alkenes

Year: 2025

Type: article

Abstract: Chiral γ-amino acids are among the most valuable and ubiquitous structural units in natural products, pharmaceuticals and many physiologically active compounds. Herein, we demonstrate a convenient synthetic approach to chiral γ-amino acid structures via an asymmetric aryl-aminoalkylation of alkenes enabled by a dual photoredox/nickel catalysis. Taking advantage of the mild and redox-neutral condition, high levels of enantiocontrol of α-carbonyl benzylic stereocenters are obtained. Experimental and computational mechanistic studies were performed to gain insights into the mechanism and origin of enantioselectivity. The results reveal that the reaction follows a Ni(0)/Ni(I)/Ni(III)/Ni(I) catalytic cycle and C‒X bond oxidative addition is the enantiodetermining step.

Source: Chinese Journal of Chemistry

DOI: 10.1002/cjoc.70060

Authors: Fu Ye, Youzhi Xu, Songlin Zheng, Genping Huang, Weiming Yuan

Institutions: Huazhong University of Science and Technology, Tianjin University, Hubei Three Gorges Laboratory

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,300

Funders: National Natural Science Foundation of China, National Key Research and Development Program of China