Chemical Resolution of C,N-Unprotected alpha-Substituted beta-Amino Acids Using Stable and Recyclable Proline-Derived Chiral Ligands
文献类型：期刊论文
| 作者 | Wang, Shuni1,2,3; Nian, Yong1,2,3; Zhou, Shengbin1,2,3; Wang, Jiang1,2,3 ; Liu, Hong1,2,3
|
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2018-09-07 |
| 卷号 | 83期号:17页码:9870-9878 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.8b01336 |
| 文献子类 | Article |
| 英文摘要 | We report the first purely chemical method for the resolution of C,N-unprotected racemic alpha-substituted beta-amino acids (beta(2)-AAs) using thermodynamically stable and recyclable chiral proline-derived ligands. The ligands and racemic beta(2)-AAs along with Ni(II) could form a pair of Ni(II) complex diastereoisomers with a desirable diastereoselectivity (dr up to 91:9). Enantiomerically pure C,N-unprotected beta(2)-AAs could be obtained by simple hydrolysis of an isolated favored Ni(II) complex. The method featured unique versatility compared with enzymatic approaches and characterized by its broad synthetic generality, good stereochemical outcome, and mild reaction conditions, thus making it a powerful supplement in the field of chemical resolution of beta(2)-AAs. |
| WOS关键词 | DYNAMIC KINETIC RESOLUTION ; ASYMMETRIC-SYNTHESIS ; BETA(2)-AMINO ACIDS ; EFFICIENT SYNTHESIS ; NI(II) COMPLEX ; ESTERS ; HOMOLOGATION ; DERIVATIVES ; PEPTIDES ; ANALOGS |
| 资助项目 | National Natural Science Foundation of China[81620108027] ; National Natural Science Foundation of China[21632008] ; National Natural Science Foundation of China[21672231] ; National Natural Science Foundation of China[21472209] ; Major Project of Chinese National Programs for Fundamental Research and Development[2015CB910304] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000444364600024 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/279585]  |
| 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 |
| 通讯作者 | Wang, Jiang; Liu, Hong |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 2.Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China; 3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Shuni,Nian, Yong,Zhou, Shengbin,et al. Chemical Resolution of C,N-Unprotected alpha-Substituted beta-Amino Acids Using Stable and Recyclable Proline-Derived Chiral Ligands[J]. JOURNAL OF ORGANIC CHEMISTRY,2018,83(17):9870-9878. |
| APA | Wang, Shuni,Nian, Yong,Zhou, Shengbin,Wang, Jiang,&Liu, Hong.(2018).Chemical Resolution of C,N-Unprotected alpha-Substituted beta-Amino Acids Using Stable and Recyclable Proline-Derived Chiral Ligands.JOURNAL OF ORGANIC CHEMISTRY,83(17),9870-9878. |
| MLA | Wang, Shuni,et al."Chemical Resolution of C,N-Unprotected alpha-Substituted beta-Amino Acids Using Stable and Recyclable Proline-Derived Chiral Ligands".JOURNAL OF ORGANIC CHEMISTRY 83.17(2018):9870-9878. |
入库方式： OAI收割
来源：上海药物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。