C α -Umpolung of Amides Strategy for Enantioselective Propargylic Amination toward C α -Tetrasubstituted α-Amino Acid Derivatives

Organic Letters 2026

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Authors: Guo-Yin Sun, Ting-Jia Sun, Wei Sun, Xue-Song Peng, Juan Liao, Yong You, Zhen-Hua Wang, Jian‐Qiang Zhao, Ming‐Qiang Zhou, Wei-Cheng Yuan
DOI: 10.1021/acs.orglett.5c05080
Cited by: 3
References: 50

Abstract

A strategy for the C α -umpolung of amides through the copper-catalyzed decarboxylation of 5-ethynyloxazolidine-2,4-diones was developed. Building on this, an asymmetric propargylic amination was achieved using primary and secondary amines as nucleophiles under cooperative catalysis of a chiral copper complex and a quinidine-derived bifunctional organocatalyst, affording a range of C α -tetrasubstituted α-amino acid derivatives in high yields with excellent enantioselectivities. The synthetic utility of this protocol was demonstrated by late-stage modification of pharmaceuticals, large-scale reactions, and versatile derivatization of products.

Fields of Study & Subjects

Advanced Synthetic Organic Chemistry Asymmetric Synthesis and Catalysis Catalytic Cross-Coupling Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
4
Pages
1276–1282
Publication date
15 January 2026
Language
EN