Enantioselective Synthesis of Chiral γ-Amino Acid Esters via Photoredox/Nickel-Catalyzed Aryl-Aminoalkylation of Alkenes
Fu Ye , Youzhi Xu , Songlin Zheng , Genping Huang , Weiming Yuan
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (15) : 1862 -1868.
Enantioselective Synthesis of Chiral γ-Amino Acid Esters via Photoredox/Nickel-Catalyzed Aryl-Aminoalkylation of Alkenes
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.
Photocatalysis / Nickel / Asymmetric synthesis / Alkenes / Amino acids
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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