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
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
收藏
页码:6799 / 6803
页数:5
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