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Rhodium-Catalyzed Diastereoselective C-H Activation/[4+2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes

文献类型：期刊论文

作者Wang, Yan2,4; Shi, Sijia2,3; Zhang, Wei2; Nian, Yong3; Wu, Xiaowei1,2,4
刊名ORGANIC LETTERS
出版日期2024-01-10
卷号26期号:2页码:483-487
ISSN号1523-7060
DOI10.1021/acs.orglett.3c03819
通讯作者Nian, Yong(ynian@njucm.edu.cn) ; Wu, Xiaowei(wuxiaowei@simm.ac.cn)
英文摘要Herein, we report a rare example of rhodium-catalyzed C-H activation/[4 + 2] annulation of alkenyl amides with bicyclic alkenes under mild and green conditions. The reactivity of the rhodium catalyst in this study differed from that observed in cobalt-catalyzed C-H activation/[3 + 2] annulation between vinylic amides and bicyclic alkenes. In addition, the reaction was performed in EtOH at room temperature, which also displayed excellent diastereoselectivity, good functional group tolerance, and air compatibility. A series of novel bridged-ring skeletons were obtained in good to excellent yields. Scale-up experiments were carried out with 1 or 0.75 mol % rhodium catalyst, affording the desired bridged-ring skeleton in excellent yields.
WOS关键词RECEPTOR PARTIAL AGONIST ; HETEROBICYCLIC ALKENES ; ALKALOIDS ; ARENES ; BOND ; DERIVATIVES ; VARENICLINE ; ALKYNES ; SKIN
资助项目National Natural Science Foundation of China[2021A1515110468] ; Basic and Applied Basic Research Foundation of Guangdong Province[21PJ1415800] ; Shanghai Pujiang Program[82204192] ; National Natural Science Foundation of China[BK20220471] ; Natural Science Foundation of Jiangsu Province[XPT82204192] ; Nanjing University of Chinese Medicine[2019B090904008] ; High-level new RD institute[2021B0909050003] ; High-level Innovative Research Institute
WOS研究方向Chemistry
语种英语
出版者AMER CHEMICAL SOC
WOS记录号WOS:001146500700001
源URL[http://119.78.100.183/handle/2S10ELR8/308963]  
专题中国科学院上海药物研究所
通讯作者Nian, Yong; Wu, Xiaowei
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Dev Ctr, Shanghai 201203, Peoples R China
2.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
3.Nanjing Univ Chinese Med, Sch Pharm, Nanjing 210023, Peoples R China
4.Guizhou Med Univ, Guizhou Prov Engn Technol Res Ctr Chem Drug R&D, Sch Pharm, Guiyang 550014, Peoples R China
推荐引用方式
GB/T 7714		 Wang, Yan,Shi, Sijia,Zhang, Wei,et al. Rhodium-Catalyzed Diastereoselective C-H Activation/[4+2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes[J]. ORGANIC LETTERS,2024,26(2):483-487.
APA Wang, Yan,Shi, Sijia,Zhang, Wei,Nian, Yong,&Wu, Xiaowei.(2024).Rhodium-Catalyzed Diastereoselective C-H Activation/[4+2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes.ORGANIC LETTERS,26(2),483-487.
MLA Wang, Yan,et al."Rhodium-Catalyzed Diastereoselective C-H Activation/[4+2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes".ORGANIC LETTERS 26.2(2024):483-487.

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来源：上海药物研究所

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