Facile synthesis and optical resolution of inherently chiral fluorescent calix[4]crowns: enantioselective recognition towards chiral leucinol

被引：75

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, Biol Chem Lab, Beijing 100080, Peoples R China

来源：

TETRAHEDRON | 2005年 / 61卷 / 35期

基金：

中国国家自然科学基金;

关键词：

calix[4]crown; inherently chiral; synthesis; optical resolution; enantioselective recognition;

D O I：

10.1016/j.tet.2005.06.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of tri-O-alkylated inherently chiral fluorescent calix[4]crowns in the cone conformations and a series of tetra-O-alkylated inherently chiral fluorescent calix[4]crowns in the partial cone conformations have been synthesized. By condensing with chiral auxiliary (S)-BINOL, the resulting diastereomers could be separated via preparative TLC. We found that the size of the crown moiety effected the separation of the diastereomers. Further, removal of the BINOL unit by hydrolysis furnished pairs of enantiomers with optical purity. Moreover, we found that a tetra-O-alkylated inherently chiral fluorescent calix[4]crown-6 in the partial cone conformation 6c showed considerable enantioselective recognition capability towards chiral leucinol. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8517 / 8528

页数：12

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