Palladium-Catalyzed Highly Enantioselective Arylation of Cyclic N-Sulfonyl alpha-Ketimino Esters towards the Synthesis of alpha-Quaternary Chiral Amino Acid Derivatives
文献类型：期刊论文
| 作者 | Wu, Chun-Yan2; Xu, Ming-Hua1,2,3
|
| 刊名 | CHEMCATCHEM
 |
| 出版日期 | 2019-12-23 |
| 页码 | 6 |
| 关键词 | alpha-quaternary chiral amino acid palladium asymmetric catalysis arylation alpha-ketimino esters |
| ISSN号 | 1867-3880 |
| DOI | 10.1002/cctc.201901933 |
| 通讯作者 | Xu, Ming-Hua(xumh@sustech.edu.cn) |
| 英文摘要 | We have developed a highly effective palladium/PHOX catalyst system for efficient asymmetric 1,2-addition of arylboronic acids to six-membered 1,2,6-thiadiazine-1,1-dioxide type cyclic N-sulfonyl alpha-iminoesters. The protocol allows convenient synthesis of a variety of nearly optically pure alpha-quaternary amino acid derivatives under mild reaction conditions. The synthetic utility of the reaction is demonstrated by simple product transformations. It allows the convenient construction of alpha,gamma-substituted chiral gamma-lactams having two carbon stereogenic centres, including one quaternary centre, in a highly enantiomerically pure form. This chemistry may be used to generate analogous molecules of BMS-561392 for bioactivity screening and drug discovery. |
| WOS关键词 | ASYMMETRIC ARYLATION ; ARYLBORONIC ACIDS ; CONSTRUCTION ; ACCESS ; AMINATION ; LIGANDS ; STEREOCENTERS ; CYCLOADDITION ; ALKYLATION ; KETOIMINES |
| 资助项目 | National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006] ; National Natural Science Foundation of China[81521005] ; National Natural Science Foundation of China[21672229] ; National Natural Science Foundation of China[21325209] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000503894000001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/282257]  |
| 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.Southern Univ Sci & Technol, Dept Chem, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wu, Chun-Yan,Xu, Ming-Hua. Palladium-Catalyzed Highly Enantioselective Arylation of Cyclic N-Sulfonyl alpha-Ketimino Esters towards the Synthesis of alpha-Quaternary Chiral Amino Acid Derivatives[J]. CHEMCATCHEM,2019:6. |
| APA | Wu, Chun-Yan,&Xu, Ming-Hua.(2019).Palladium-Catalyzed Highly Enantioselective Arylation of Cyclic N-Sulfonyl alpha-Ketimino Esters towards the Synthesis of alpha-Quaternary Chiral Amino Acid Derivatives.CHEMCATCHEM,6. |
| MLA | Wu, Chun-Yan,et al."Palladium-Catalyzed Highly Enantioselective Arylation of Cyclic N-Sulfonyl alpha-Ketimino Esters towards the Synthesis of alpha-Quaternary Chiral Amino Acid Derivatives".CHEMCATCHEM (2019):6. |
入库方式： OAI收割
来源：上海药物研究所
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