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Enantioselective Radical Addition of Carboxylic Acids to Imines through Cooperative Copper/Acridine Catalysis

文献类型：期刊论文

作者Huang, Haihui1,2; Xia, Guoqin1
刊名JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
出版日期2026-01-28
卷号148期号:3页码:3884-3893
ISSN号0002-7863
DOI10.1021/jacs.5c22180
通讯作者Xia, Guoqin(xiaguoqin@simm.ac.cn)
英文摘要Amino acids and their derivatives are indispensable as both synthetic building blocks and functional entities in the chemical industry and life sciences. Herein, we report a modular strategy for the asymmetric synthesis of chiral alpha-amino acids and amines through the decarboxylative radical addition to imines. This protocol leverages readily available, cost-effective carboxylic acids, aldehydes, and anilines as starting materials, enabled by the synergistic catalysis of acridine and copper. The reaction operates under ambient conditions, exhibits excellent functional group compatibility, and delivers high stereocontrol across a diverse substrate scope. Notably, it allows for the stereodivergent installation of multiple chiral centers into amino acid derivatives. Preliminary mechanistic investigations support a pathway involving the direct radical addition to the imine. This method thus provides a robust and reliable platform for accessing chiral amino acids and amines.
WOS关键词ALPHA-AMINO-ACIDS ; ASYMMETRIC-SYNTHESIS ; STEREOSELECTIVE AMINATION ; DERIVATIVES ; ALKYLATION ; HYDRAZINO ; HCN
资助项目National Natural Science Foundation of China (NSFC)[22271297] ; Zhongshan Science and Technology Bureau[CXTD2023009]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001661058600001
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/322628]  
专题中国科学院上海药物研究所
通讯作者Xia, Guoqin
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, Zhongshan Inst Drug Discovery, Zhongshan 528400, Peoples R China
2.Guangzhou Univ Chinese Med, Guangzhou 510006, Peoples R China
推荐引用方式
GB/T 7714		 Huang, Haihui,Xia, Guoqin. Enantioselective Radical Addition of Carboxylic Acids to Imines through Cooperative Copper/Acridine Catalysis[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2026,148(3):3884-3893.
APA Huang, Haihui,&Xia, Guoqin.(2026).Enantioselective Radical Addition of Carboxylic Acids to Imines through Cooperative Copper/Acridine Catalysis.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,148(3),3884-3893.
MLA Huang, Haihui,et al."Enantioselective Radical Addition of Carboxylic Acids to Imines through Cooperative Copper/Acridine Catalysis".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 148.3(2026):3884-3893.

入库方式： OAI收割

来源：上海药物研究所

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