Syntheses of chiral homoazacalix[4]arenes incorporating amino acid residues: Molecular recognition for racemic quaternary ammonium ions

被引：48

作者：

Ito, K ^{[1
]}

Noike, M ^{[1
]}

Kida, A ^{[1
]}

Ohba, Y ^{[1
]}

机构：

[1] Yamagata Univ, Dept Chem & Chem Engn, Fac Engn, Yonezawa, Yamagata 9928510, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 21期

关键词：

D O I：

10.1021/jo020300u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral calixarene analogues incorporating amino acid residues into the macrocyclic rings were prepared from the cyclization reactions of bis(chloromethyl)phenol-formaldehyde tetramer with amino acid methyl ester in moderate yields. The macrocycles form a chiral concavity, which is induced by the chiral transmission from the point chirality of the amino acid residues to the phenol-formaldehyde tetramer unit. The macrocycles have the cavity pi-basic enough to include the quaternary ammonium ion due to the cation-pi interaction and can serve as a shift reagent for racemic ammonium ions during H-1 NMR analysis.

引用

页码：7519 / 7522

页数：4

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