Synthesis of new chiral imidazolium salts derived from amino acids: their evaluation in chiral molecular recognition

被引:38
作者
Altava, Belen [1 ]
Barbosa, Dalgi S. [1 ]
Isabel Burguete, M. [1 ]
Escorihuela, Jorge [1 ]
Luis, Santiago V. [1 ]
机构
[1] Univ Jaume 1, Dept Quim Inorgan & Organ, Castellon de La Plana 12071, Spain
关键词
IONIC LIQUIDS; CHROMATOGRAPHIC SEPARATION; NMR ENANTIODISCRIMINATION; CARBOXYLIC-ACIDS; SOLVATING AGENTS; SHIFT-REAGENT; DESIGN; OPTIMIZATION; RECEPTORS; VERSATILE;
D O I
10.1016/j.tetasy.2009.03.028
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A family of new imidazolium salts derived from natural amino acids has been synthesized and tested for NMR enantiodiscrimination, as chiral shift reagents, of carboxylic acids. These imidazolium receptors contain different Structural modifications and the splitting of the signals of the acids, after addition of the corresponding CSRs, depends on these structural variables. Compound 8b exhibited the strongest chiral solvating properties for racemic Mosher acid and was recognized as a suitable CSR for the determination of its enantiomeric composition. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:999 / 1003
页数:5
相关论文
共 48 条
[1]  
Altava B, 1999, EUR J ORG CHEM, V1999, P2263
[2]  
Altava B, 1997, AN QUIM, V93, P260
[3]  
[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014
[4]   Synthesis of chiral ionic liquids from natural amino acids [J].
Bao, WL ;
Wang, ZM ;
Li, YX .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :591-593
[5]  
Baragaña B, 2002, CHEM-EUR J, V8, P2931, DOI 10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO
[6]  
2-H
[7]   Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].
Baudequin, C ;
Brégeon, D ;
Levillain, J ;
Guillen, F ;
Plaquevent, JC ;
Gaumont, AC .
TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945
[8]   Ionic liquids and chirality: opportunities and challenges [J].
Baudequin, C ;
Baudoux, J ;
Levillain, J ;
Cahard, D ;
Gaumont, AC ;
Plaquevent, JC .
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093
[9]  
Bladon C., 2002, Pharmaceutical Chemistry: Therapeutic Aspects of Biomacromolecules
[10]   Guanidinium receptors as enantioselective amino acid membrane carriers [J].
Breccia, P ;
Van Gool, M ;
Pérez-Fernández, R ;
Martín-Santamaría, S ;
Gago, F ;
Prados, P ;
de Mendoza, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8270-8284