Enantioselective fluorescent recognition of chiral acids by 3- and 3,3′-aminomethyl substituted BINOLs

被引：40

作者：

Lin, J ^{[1
]}

Rajararn, AR ^{[1
]}

Pu, L ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 49期

基金：

美国国家卫生研究院;

关键词：

enantioselective; fluorescent sensors; mandelic acid; amino acids; BINOL;

D O I：

10.1016/j.tet.2004.08.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzylaminomethyl groups are introduced to the 3,3'-positions of BINOL. The resulting compounds can be used to conduct the enantioselective fluorescent recognition of mandelic acid and N-benzyloxycarbonylphenylglycine. ln the presence of (S)-mandelic acid, compound (R)-2 showed over 30-fold fluorescence enhancement with the ef [ef=enantiomeric fluorescence difference ratio=(I-s-I-0)/(I-R-I-0)] up to 4.2. In the presence of D-N- benzyloxycarbonylphenylglycine, compound (RR)-4 showed up to 15-fold fluorescence enhancement with the ef up to 5.0. These high fluorescence sensitivity and enantioselectivity make compounds (R)-2 and (RR)-4 practically useful sensors for the recognition of the chiral acids in apolar solvents. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：11277 / 11281

页数：5

共 13 条

[1] MACROCYCLES CONTAINING TIN - PREPARATION OF MACROBICYCLIC LEWIS ACIDIC HOSTS CONTAINING 2 TIN ATOMS AND SN-119 NMR-STUDIES OF THEIR CHLORIDE AND BROMIDE BINDING-PROPERTIES IN SOLUTION [J].