Rhodium(I) Carbene-Promoted Enantioselective C-H Functionalization of Simple Unprotected Indoles, Pyrroles and Heteroanalogues: New Mechanistic Insights
文献类型：期刊论文
| 作者 | Wang, Tian-Yi1,2,3,4; Chen, Xiao-Xuan3,4; Zhu, Dong-Xing1,2; Chung, Lung Wa3,4; Xu, Ming-Hua1,2,3,4,5
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| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2022-08-22 |
| 卷号 | 61期号:34页码:e202207008 |
| 关键词 | Asymmetric Catalysis C-H Functionalization Carbene Insertion Chiral Diene Unprotected Indoles |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.202207008 |
| 文献子类 | Article |
| 英文摘要 | A rhodium(I)-diene catalyzed highly enantioselective C(sp(2))-H functionalization of simple unprotected indoles, pyrroles, and their common analogues such as furans, thiophenes, and benzofurans with arylvinyldiazoesters has been developed for the first time. This transformation features unusual site-selectivity exclusively at the vinyl terminus of arylvinylcarbene and enables a reliable and rapid synthetic protocol to access a distinctive class of diarylmethine-bearing alpha,beta-unsaturated esters containing a one or two heteroarene-attached tertiary carbon stereocenter in high yields and excellent enantioselectivities under mild reaction conditions. Mechanistic studies and DFT calculations suggest that, compared to the aniline substrate, the more electron-rich indole substrate lowers the C-C addition barrier and alters the rate-determining step to the reductive elimination, leading to different isotope effect. |
| WOS关键词 | INSERTION ; BOND ; DERIVATIVES ; ACTIVATION ; ACCESS |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000821522700001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/309326]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Xu, Ming-Hua |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 2.Univ Chinese Acad Sci, Sch Pharm, Shanghai 201203, Peoples R China; 3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China; 4.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China; 5.Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Tian-Yi,Chen, Xiao-Xuan,Zhu, Dong-Xing,et al. Rhodium(I) Carbene-Promoted Enantioselective C-H Functionalization of Simple Unprotected Indoles, Pyrroles and Heteroanalogues: New Mechanistic Insights[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022,61(34):e202207008. |
| APA | Wang, Tian-Yi,Chen, Xiao-Xuan,Zhu, Dong-Xing,Chung, Lung Wa,&Xu, Ming-Hua.(2022).Rhodium(I) Carbene-Promoted Enantioselective C-H Functionalization of Simple Unprotected Indoles, Pyrroles and Heteroanalogues: New Mechanistic Insights.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,61(34),e202207008. |
| MLA | Wang, Tian-Yi,et al."Rhodium(I) Carbene-Promoted Enantioselective C-H Functionalization of Simple Unprotected Indoles, Pyrroles and Heteroanalogues: New Mechanistic Insights".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 61.34(2022):e202207008. |
入库方式： OAI收割
来源：上海药物研究所
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