Synthesis of new chiral calix[4]azacrowns for enantiomeric recognition of carboxylic acids

被引：21

作者：

Demirtas, Havva Nur ^{[1
]}

Bozkurt, Selahattin ^{[1
]}

Durmaz, Mustafa ^{[1
]}

Yilmaz, Mustafa ^{[1
]}

Sirit, Abdulkadir ^{[1
]}

机构：

[1] Selcuk Univ, Dept Chem, TR-42099 Konya, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 17期

关键词：

D O I：

10.1016/j.tetasy.2008.08.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two novel chiral calix[4]azacrown ethers 4 and 5 bearing a furfuryl group on the nitrogen atom were developed by the reaction of dibromo- or ditosyl derivatives of p-tert-butylcalix[4]arenes 2 and 3 with a chiral diol, 1. The enantioselective recognition of these receptors towards the enantiomers of racemic carboxylic acids has been studied by H-1 NMR spectroscopy. The molar ratio and the association constants of the chiral compounds 4 and 5 with each of the enantiomers of guest molecules were determined by using job plots and a nonlinear least-squares fitting method, respectively. The job plots indicate that both of the hosts form 1:1 instantaneous complexes with (R)- OF (S)-mandelic acid and (L)- or (D)-dibenzoyl-tartaric acid. The receptors exhibited different chiral recognition abilities towards the enantiomers of racemic guests. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2020 / 2025

页数：6

共 71 条

[1] Chiral recognition of alpha-amino acid derivatives with a homooxacalix[3]arene: Construction of a pseudo-C-2-symmetrical compound from a C-3-symmetrical macrocycle [J].