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Diastereoselective Radical Cyclization of Imine and Olefin: Rapid Access to 1,2,3,4-Tetrahydroquinoline Scaffolds

文献类型：期刊论文

作者Zhang, Suping3; Zeng, Tianyan3; Huang, Haihui3; Wang, Yuguo4; Cao, Wenxu1,2; Babu, G. V. Surendra2; Li, Jia2,4; Zhang, Pengli2; Wang, Mingliang2,3; Xia, Guoqin1,2,3
刊名ORGANIC LETTERS
出版日期2025-05-06
卷号27期号:19页码:4946-4951
ISSN号1523-7060
DOI10.1021/acs.orglett.5c01242
通讯作者Li, Jia(jli@simm.ac.cn) ; Zhang, Pengli(zhangpengli@zidd.ac.cn) ; Wang, Mingliang(wangmingliang@simm.ac.cn) ; Xia, Guoqin(xiaguoqin@simm.ac.cn)
英文摘要Herein, we developed an intramolecular radical cyclization reaction between imines (or aldehydes) and olefins using Hantzsch ester as the reductant to enable the efficient and diastereoselective synthesis of 1,2,3,4-tetrahydroquinoline scaffolds with a high medicinal value. Deuteration experiments indicated that the radical intermediate abstracts a hydrogen atom directly from the 4 position of the Hantzsch ester, thereby ruling out the possibility of an anionic intermediate formation via the radical crossover pathway. A fast synthesis of BRD4 degraders and the elucidation of their cellular and enzymatic activities demonstrate the practicality of this method.
WOS关键词COUPLED ELECTRON-TRANSFER ; PHOTOREDOX CATALYSIS ; ENANTIOSELECTIVE SYNTHESIS ; TRANSFER HYDROGENATION ; ASYMMETRIC-SYNTHESIS ; ACID ; DERIVATIVES ; POVAROV
资助项目National Natural Science Foundation of China[22271297] ; National Natural Science Foundation of China[2021QN020533] ; Program for Talented Young Investigators of Guangdong Province[CXTD2023009] ; Zhongshan Science and Technology Bureau
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001484545300001
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/317605]  
专题中国科学院上海药物研究所
通讯作者Li, Jia; Zhang, Pengli; Wang, Mingliang; Xia, Guoqin
作者单位1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Guangdong, Peoples R China
3.Guangzhou Univ Chinese Med, Guangzhou 510006, Peoples R China
4.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210000, Peoples R China
推荐引用方式
GB/T 7714		 Zhang, Suping,Zeng, Tianyan,Huang, Haihui,et al. Diastereoselective Radical Cyclization of Imine and Olefin: Rapid Access to 1,2,3,4-Tetrahydroquinoline Scaffolds[J]. ORGANIC LETTERS,2025,27(19):4946-4951.
APA Zhang, Suping.,Zeng, Tianyan.,Huang, Haihui.,Wang, Yuguo.,Cao, Wenxu.,...&Xia, Guoqin.(2025).Diastereoselective Radical Cyclization of Imine and Olefin: Rapid Access to 1,2,3,4-Tetrahydroquinoline Scaffolds.ORGANIC LETTERS,27(19),4946-4951.
MLA Zhang, Suping,et al."Diastereoselective Radical Cyclization of Imine and Olefin: Rapid Access to 1,2,3,4-Tetrahydroquinoline Scaffolds".ORGANIC LETTERS 27.19(2025):4946-4951.

入库方式： OAI收割

来源：上海药物研究所

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