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Stereoselective Radical Cross-Coupling of Amino Acids and Imines via Hydrogen-Bond Catalysis

文献类型：期刊论文

作者Shu, Wen1,2; Cao, Wenxu1; Zhang, Suping1; Huang, Haihui1; Song, Xiaorong1; Zhang, Pengli1; Xia, Guoqin1,2
刊名ACS CATALYSIS
出版日期2025-12-19
卷号15期号:24页码:21033-21041
关键词radical cross-coupling stereoselective hydrogen-bondcatalysis photocatalysis 1,2-diamine
ISSN号2155-5435
DOI10.1021/acscatal.5c07372
通讯作者Zhang, Pengli(zhangpengli@zidd.ac.cn) ; Xia, Guoqin(xiaguoqin@simm.ac.cn)
英文摘要Stereochemical control remains one of the most challenging obstacles in developing practical radical transformations. Recent progress in transition-metal-catalyzed radical reactions has shed light on methods for stereoselectively constructing C(sp3)-C(sp3) bonds through a single electron transfer mechanism. However, the field of chiral Br & oslash;nsted acid-catalyzed stereoselective radical reactions is relatively less studied. Herein, we present a stereoselective radical cross-coupling between abundant amino acids and readily available imine substrates (prepared in situ from aldehydes and anilines) via cooperative catalysis of photoredox and phosphoric acid. This method features good functional group compatibility, providing a diverse range of chiral 1,2-diamine products which are valuable in synthetic utility. Preliminary mechanistic studies indicate that this reaction probably proceeds via both radical-radical cross-coupling pathway and radical nucleophilic addition mechanism.
WOS关键词CHIRAL N-ACYLHYDRAZONES ; ASYMMETRIC DIAMINATION ; VICINAL DIAMINATION ; BRONSTED ACID ; PHOTOREDOX ; DIAZIDATION ; HYDRAZONES ; COMPLEXES ; ALKENES ; OLEFINS
资助项目Chinese Academy of Sciences[NA] ; Program for Talented Young Investigators of Guangdong Province[2021QN020533] ; National Natural Science Foundation of China[22271297]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001632747900001
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/322348]  
专题中国科学院上海药物研究所
通讯作者Zhang, Pengli; Xia, Guoqin
作者单位1.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
2.Macau Univ Sci & Technol, Sch Pharm, Lab Drug Discovery Nat Resources & Industrializat, State Key Lab Mech & Qual Chinese Med, Taipa 999078, Macao, Peoples R China
推荐引用方式
GB/T 7714		 Shu, Wen,Cao, Wenxu,Zhang, Suping,et al. Stereoselective Radical Cross-Coupling of Amino Acids and Imines via Hydrogen-Bond Catalysis[J]. ACS CATALYSIS,2025,15(24):21033-21041.
APA Shu, Wen.,Cao, Wenxu.,Zhang, Suping.,Huang, Haihui.,Song, Xiaorong.,...&Xia, Guoqin.(2025).Stereoselective Radical Cross-Coupling of Amino Acids and Imines via Hydrogen-Bond Catalysis.ACS CATALYSIS,15(24),21033-21041.
MLA Shu, Wen,et al."Stereoselective Radical Cross-Coupling of Amino Acids and Imines via Hydrogen-Bond Catalysis".ACS CATALYSIS 15.24(2025):21033-21041.

入库方式： OAI收割

来源：上海药物研究所

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