Enantioselective recognition of amines with an atropisomeric 1,8-bisphenolnaphthalene

被引：16

作者：

Ghosn, Marwan W. ^{[1
]}

Wolf, Christian ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

TETRAHEDRON | 2011年 / 67卷 / 36期

基金：

美国国家科学基金会;

关键词：

Atropisomers; 1,8-Bisphenolnaphthalenes; Dynamic stereochemistry; Enantioselective recognition; Circular dichroism; ENANTIOMERIC EXCESS; FLUORESCENT SENSORS; CARBOXYLIC-ACIDS; CHIRAL COMPOUNDS; STEREODYNAMICS; CATALYSIS; DYNAMICS; FACILE; BINOL;

D O I：

10.1016/j.tet.2011.07.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,8-Bis[5'(2'-hydroxy-4'-methylbiPhenyl)]naphthalene, 2, was prepared from 1,8-dibromonaphthalene and 4-methoxy-2-methylphenylboronic acid in four steps with 51% overall yield. The axially chiral anti-isomer of 2 is stable to racemization at room temperature and the free energy of activation for the conversion of the anti-isomer to the syn-form was determined as 110.0 kJ/mol at 77.1 degrees C. At submillimolar concentration, enantiopure 2 can be used as circular dichroism sensor to detect a wide range of chiral amines. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6799 / 6803

页数：5

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