Efficient synthesis and resolution of meta-substituted inherently chiral aminocalix[4]arene derivatives
文献类型：期刊论文
| 作者 | Xu ZhenXiang; Zhang Chun; Huang ZhiTang; Chen ChuanFeng |
| 刊名 | CHINESE SCIENCE BULLETIN
 |
| 出版日期 | 2010-09-01 |
| 卷号 | 55期号:25页码:2859-2869 |
| 关键词 | Inherently Chiral Calixarenes Kinetic Resolution Synthesis |
| ISSN号 | 1001-6538 |
| DOI | 10.1007/s11434-010-3121-8 |
| 英文摘要 | Efficient synthesis and resolution of a series of meta-substituted inherently chiral aminocalix[4]arene derivatives have been described. Consequently, the meta-nitro, bromo and chloro substituted inherently chiral calix[4]arenes could be directly synthesized by the nitration, bromination, and chlorination of the acylating product of aminocalix[4]arene. meta-Cyano and phenyl substituted inherently chiral aminocalix[4]arenes were readily obtained by the nucleophilic substitution reaction or Suzuki coupling reaction from the meta-bromo substituted one under the Pd-catalyzed conditions. For kinetic resolution of the racemic inherently chiral aminocalix[4]arenes, it was found that the electron-withdrawing ability of substituent was helpful to improving the resolution efficiency of the acylation process, and the kinetic resolution could be efficiently applied to the resolution of meta-nitro substituted inherently chiral aminocalix[4]arene, providing (cS)- or (cR)-isomer in up to 95% or 99.9% ee value, respectively, with the corresponding chiral acylating reagent. Moreover, by introduction of the chiral auxiliary, enantiopure antipodes of meta-cyano and phenyl substituted inherently chiral aminocalix[4]arenes could also be readily obtained. These enantiopure aminocalix[4]arenes are potential building blocks for constructing novel chiral receptors and asymmetric catalysts. |
| 语种 | 英语 |
| WOS记录号 | WOS:000281695100019 |
| 出版者 | SCIENCE PRESS |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/69103]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Chen ChuanFeng |
| 作者单位 | Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xu ZhenXiang,Zhang Chun,Huang ZhiTang,et al. Efficient synthesis and resolution of meta-substituted inherently chiral aminocalix[4]arene derivatives[J]. CHINESE SCIENCE BULLETIN,2010,55(25):2859-2869. |
| APA | Xu ZhenXiang,Zhang Chun,Huang ZhiTang,&Chen ChuanFeng.(2010).Efficient synthesis and resolution of meta-substituted inherently chiral aminocalix[4]arene derivatives.CHINESE SCIENCE BULLETIN,55(25),2859-2869. |
| MLA | Xu ZhenXiang,et al."Efficient synthesis and resolution of meta-substituted inherently chiral aminocalix[4]arene derivatives".CHINESE SCIENCE BULLETIN 55.25(2010):2859-2869. |
入库方式： OAI收割
来源：化学研究所
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