Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives
文献类型：期刊论文
| 作者 | Li, Yi; Yu, Yue-Na; Xu, Ming-Hua
|
| 刊名 | ACS CATALYSIS
 |
| 出版日期 | 2016-02 |
| 卷号 | 6期号:2页码:661-665 |
| 关键词 | asymmetric catalysis rhodium arylation cyclic ketimine P-olefin ligand alpha-amino acid |
| ISSN号 | 2155-5435 |
| DOI | 10.1021/acscatal.5b02403 |
| 文献子类 | Article |
| 英文摘要 | A new class of open-chain chiral phosphite based hybrid olefin ligands has been developed and utilized in Rh-catalyzed asymmetric arylation of 1,2,5-thiadiazolidine 1,1-dioxide type cyclic ketimines. The reactions generate quaternary carbon-containing, gem-diaryl-substituted sulfahydantoins and 4-ethoxy-2,3-dihydro-1,2,S-thiadiazole 1,1-dioxides with excellent enantioselectivities under exceptionally mild and user-friendly conditions using a H-8-binol-derived phosphite-olefin ligand. The method is useful in offering efficient and convenient synthesis of enantioriched alpha,alpha-diaryl-alpha-amino acid amides and nitrogen-containing heterocycles. Furthermore, by taking advantage of the protocol, the first enantioselective synthesis of BACE1 inhibitor (R)-iminohydantoin has been accomplished. |
| WOS关键词 | N-SULFONYL KETIMINES ; MECHANISM-BASED INHIBITORS ; STRUCTURE-BASED DESIGN ; ARYL BORONIC ACIDS ; EFFICIENT SYNTHESIS ; ARYLBORONIC ACIDS ; NUCLEOPHILIC ALLYLATION ; BACE1 INHIBITORS ; SULFUR-OLEFINS ; CHIRAL LIGANDS |
| 资助项目 | National Science Foundation of China[21325209] ; National Science Foundation of China[21472205] ; Shanghai Municipal Committee of Science and Technology (Program of Shanghai Academic Research Leader)[14XD1404400] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000369774900020 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276161]  |
| 专题 | 药物化学研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 药物靶标结构与功能中心 |
| 通讯作者 | Xu, Ming-Hua |
| 作者单位 | Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Yi,Yu, Yue-Na,Xu, Ming-Hua. Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives[J]. ACS CATALYSIS,2016,6(2):661-665. |
| APA | Li, Yi,Yu, Yue-Na,&Xu, Ming-Hua.(2016).Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives.ACS CATALYSIS,6(2),661-665. |
| MLA | Li, Yi,et al."Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives".ACS CATALYSIS 6.2(2016):661-665. |
入库方式： OAI收割
来源：上海药物研究所
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