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ShanghaiTech University Knowledge Management System
| Construction of Si-Stereogenic Silanols by Palladium-Catalyzed Enantioselective C−H Alkenylation | |
| 2024 | |
| 发表期刊 | ANGEWANDTE CHEMIE - INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year]) |
| ISSN | 1433-7851 |
| EISSN | 1521-3773 |
| 卷号 | 63期号:20 |
| 发表状态 | 已发表 |
| DOI | 10.1002/anie.202402612 |
| 摘要 | The construction of silicon-stereogenic silanols via Pd-catalyzed intermolecular C−H alkenylation with the assistance of a commercially available L-pyroglutamic acid has been realized for the first time. Employing oxime ether as the directing group, silicon-stereogenic silanol derivatives could be readily prepared with excellent enantioselectivities, featuring a broad substrate scope and good functional group tolerance. Moreover, parallel kinetic resolution with unsymmetric substrates further highlighted the generality of this protocol. Mechanistic studies indicate that L-pyroglutamic acid could stabilize the Pd catalyst and provide excellent chiral induction. Preliminary computational studies unveil the origin of the enantioselectivity in the C−H bond activation step. © 2024 Wiley-VCH GmbH. |
| 关键词 | Catalysis Enantioselectivity Organic acids Silicon compounds Substrates C−H alkenylation Directing groups Enantioselective MPAA ligand Oxime ethers Palladium-catalyzed Parallel kinetic resolution Pyroglutamic acids Silanols Silicon-stereogenic |
| URL | 查看原文 |
| 收录类别 | EI ; SCI |
| 语种 | 英语 |
| 资助项目 | National Natural Science Foundation of China["22371293","22101291","22171277","21821002"] ; Strategic Priority Research Program of the Chinese Academy of Sciences[XDB0610000] ; Program of Shanghai Academic/Technology Research Leader[23XD1424500] ; null[2021YFA1500200] |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Multidisciplinary |
| WOS记录号 | WOS:001186421700001 |
| 出版者 | John Wiley and Sons Inc |
| EI入藏号 | 20241215771658 |
| EI主题词 | Palladium |
| EI分类号 | 547.1 Precious Metals ; 801.4 Physical Chemistry ; 802.2 Chemical Reactions ; 804.1 Organic Compounds |
| 原始文献类型 | Article in Press |
| 引用统计 | 正在获取...
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| 文献类型 | 期刊论文 |
| 条目标识符 | https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/359894 |
| 专题 | 物质科学与技术学院 物质科学与技术学院_硕士生 |
| 通讯作者 | Wang, Peng |
| 作者单位 | 1.State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS, 345 Lingling Road, Shanghai; 200032, China; 2.School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou; 310024, China; 3.College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Zhejiang, Hangzhou; 311121, China; 4.School of Physical Science and Technology, ShanghaiTech University, Shanghai; 201210, China |
| 第一作者单位 | 物质科学与技术学院 |
| 推荐引用方式 GB/T 7714 | Zhao, Jia-Hui,Zheng, Long,Zou, Jian-Ye,et al. Construction of Si-Stereogenic Silanols by Palladium-Catalyzed Enantioselective C−H Alkenylation[J]. ANGEWANDTE CHEMIE - INTERNATIONAL EDITION,2024,63(20). |
| APA | Zhao, Jia-Hui.,Zheng, Long.,Zou, Jian-Ye.,Zhang, Sheng-Ye.,Shen, Hua-Chen.,...&Wang, Peng.(2024).Construction of Si-Stereogenic Silanols by Palladium-Catalyzed Enantioselective C−H Alkenylation.ANGEWANDTE CHEMIE - INTERNATIONAL EDITION,63(20). |
| MLA | Zhao, Jia-Hui,et al."Construction of Si-Stereogenic Silanols by Palladium-Catalyzed Enantioselective C−H Alkenylation".ANGEWANDTE CHEMIE - INTERNATIONAL EDITION 63.20(2024). |
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