Design and synthesis of imidazolinium salts derived from (L)-valine. Investigation of their potential in chiral molecular recognition

被引:116
作者
Clavier, H
Boulanger, L
Audic, N
Toupet, L
Mauduit, M [1 ]
Guillemin, JC
机构
[1] Ecole Natl Super Chim Rennes, Inst Chim Rennes, CNRS, UMR 6052, F-35700 Rennes, France
[2] Univ Rennes 1, CNRS, UMR 6626, F-35700 Rennes, France
关键词
D O I
10.1039/b402368d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several imidazolinium salts are synthesized from (L)-valine. A study of the structure relationships is achieved to obtain high diastereomeric interactions with an anionic substrate. High splitting up to 60 Hz of the (rac)-potassium Mosher's salt are observed by NMR spectroscopy.
引用
收藏
页码:1224 / 1225
页数:2
相关论文
共 18 条
  • [1] Anastas P. T., 1999, GREEN CHEM FRONTIERS
  • [2] Synthesis of chiral ionic liquids from natural amino acids
    Bao, WL
    Wang, ZM
    Li, YX
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) : 591 - 593
  • [3] Ionic liquids and chirality: opportunities and challenges
    Baudequin, C
    Baudoux, J
    Levillain, J
    Cahard, D
    Gaumont, AC
    Plaquevent, JC
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (20) : 3081 - 3093
  • [4] Ionic liquid (molten salt) phase organometallic catalysis
    Dupont, J
    de Souza, RF
    Suarez, PAZ
    [J]. CHEMICAL REVIEWS, 2002, 102 (10) : 3667 - 3691
  • [5] Dupont J, 2000, CHEM-EUR J, V6, P2377, DOI 10.1002/1521-3765(20000703)6:13<2377::AID-CHEM2377>3.3.CO
  • [6] 2-C
  • [7] ASYMMETRIC INDUCTION IN THE BAYLIS-HILLMAN REACTION
    GILBERT, A
    HERITAGE, TW
    ISAACS, NS
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (10) : 969 - 972
  • [8] Design and synthesis of a novel imidazolium-based ionic liquid with planar chirality
    Ishida, Y
    Miyauchi, H
    Saigo, K
    [J]. CHEMICAL COMMUNICATIONS, 2002, (19) : 2240 - 2241
  • [9] Convenient syntheses of unsymmetrical imidazolidines
    Katritzky, AR
    Suzuki, K
    He, HY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) : 3109 - 3114
  • [10] Synthesis and properties of thiazoline based ionic liquids derived from the chiral pool
    Levillain, J
    Dubant, G
    Abrunhosa, I
    Gulea, M
    Gaumont, AC
    [J]. CHEMICAL COMMUNICATIONS, 2003, (23) : 2914 - 2915