Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives

被引：53

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 | 2009年 / 65卷 / 15期

关键词：

CATION-PI INTERACTIONS; ALKALI-METAL IONS; MOLECULAR RECOGNITION; DIAMIDE DERIVATIVES; SYNTHETIC RECEPTORS; CARBOXYLIC-ACIDS; COMPLEXATION; CALIXARENES; 2,4,6-TRIAMINOPYRIMIDINE; CONFORMATION;

D O I：

10.1016/j.tet.2009.01.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

in this study the synthesis of novel chiral calix[4]azacrown derivatives has been reported. The enantioselectivity of Chiral receptors was investigated by using UV-vis spectroscopy. All the chiral calix[4]arene derivative,; exhibited certain chiral recognition toward the enantiomers of phenylalanine (Phe-OMe.HCl) and alanine methyl ester hydrochlorides (Ala-OME.HCl). As a chiral receptor, the furfuryl-armed calix[4]azacrown ether 7 has the best enantiomeric discriminating ability for alpha-amino acid ester hydrochlorides (up to K-L/K-D 2.08, Delta Delta G(0) 1.82 KJ mol (1)) in CHCl3. The enantiomeric recognition abilities for 1,guests are also discussed from a thermodynamic point of view. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3014 / 3018

页数：5

共 46 条

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