Synthesis and optical resolution of a series of inherently chiral calix[4]crowns with cone and partial cone conformations

被引：53

作者：

Luo, J ^{[1
]}

Zheng, QY ^{[1
]}

Chen, CF ^{[1
]}

Huang, ZT ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 20期

关键词：

calixarenes; chirality; crown compounds; optical resolution; synthesis;

D O I：

10.1002/chem.200500272

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of inherently chiral calix[4]arenes with cone and partial cone conformations and with crown ether moieties of variable size have been readily synthesized. By taking advantage of the carboxy appendage on the lower rim, these were condensed with the chiral auxiliary (S)-BINOL to form diastereomers which, in most cases, could be separated by preparative TLC, or more desirably, by column chromatography on silica gel (diastereomeric excess > 99% based on HPLC analysis). Seven enantiopure antipodes of inherently chiral calix[4]crowns were obtained after hydrolysis. It has been found that both the size of the crown moiety and alkylation of the last phenolic hydroxy group (accompanied with or without a change in the conformation) affect the separation of the diastereomers.

引用

页码：5917 / 5928

页数：12

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