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 50 条
  • [1] Chiral Imidazolium Salts Derived from Amino Acids: Synthesis Characterization and Structure
    Quinonez-Lopez, Raul R.
    Idalia Rangel-Salas, I.
    Roberto Estrada-Flores, J.
    Cortes-Llamas, Sara A.
    Gallegos-Castillo, Saul
    [J]. CURRENT ORGANIC CHEMISTRY, 2018, 22 (26) : 2589 - 2597
  • [2] Imidazolium salts from amino acids-a new route to chiral zwitterionic carbene precursors?
    Kuehl, Olaf
    Palm, Gottfried
    [J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (04) : 393 - 397
  • [3] Synthesis of Chiral Room Temperature Ionic Liquids from Amino Acids - Application in Chiral Molecular Recognition
    Gonzalez, Laura
    Altava, Belen
    Bolte, Michael
    Burguete, M. Isabel
    Garcia-Verdugo, Eduardo
    Luis, Santiago V.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (26) : 4996 - 5009
  • [4] Synthesis of chiral diaza 18-crown-6 ethers from chiral amines and molecular recognition of potassium and sodium salts of amino acids
    Demirel, N
    Bulut, Y
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (17) : 2633 - 2637
  • [5] Design and synthesis of novel chiral imidazolium cyclophanes and their enantioselective recognition for α-amino acids and their derivatives
    Guo Sheng-Jin
    Luo Kui
    Wang Wen-Hai
    Zhang Shi-Yong
    Jiang He-Yan
    Lan Jing-Bo
    Xie Ru-Gang
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2006, 27 (09): : 1664 - 1668
  • [6] Design and synthesis of novel chiral imidazolium cyclophanes and their enantioselective recognition for α-amino acids and their derivatives
    Guo, Sheng-Jin
    Luo, Kui
    Wang, Wen-Hai
    Zhang, Shi-Yong
    Jiang, He-Yan
    Lan, Jing-Bo
    Xie, Ru-Gang
    [J]. Gaodeng Xuexiao Huaxue Xuebao/Chemical Journal of Chinese Universities, 2006, 27 (09): : 1664 - 1668
  • [7] A modular synthesis of chiral aminoindanol-derived imidazolium salts
    Struble, Justin R.
    Bode, Jeffrey W.
    [J]. TETRAHEDRON, 2008, 64 (29) : 6961 - 6972
  • [8] Synthesis and characterization of chiral imidazolium salts
    Machado, MY
    Dorta, R
    [J]. SYNTHESIS-STUTTGART, 2005, (15): : 2473 - 2475
  • [9] A new strategy for chiral recognition of amino acids
    Fu, Yingzi
    Han, Qian
    Chen, Qiao
    Wang, Yonghua
    Zhou, Juan
    Zhang, Qing
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (17) : 2322 - 2324
  • [10] SYNTHESIS OF CHIRAL THIOCARBAMOYLPHOSPHINES DERIVED FROM AMINO-ACIDS
    KUNZE, U
    BURGHARDT, R
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 29 (2-4): : 373 - 376