New chiral ionic liquids based on imidazolinium salts

被引:33
|
作者
Winkel, Andreas [1 ]
Wilhelm, Rene [1 ]
机构
[1] Clausthal Univ Technol, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany
关键词
DIELS-ALDER REACTION; GRIGNARD-REAGENTS; SHIFT-REAGENTS; AMINO-ACID; DESIGN; RECOGNITION; CHEMISTRY; CATALYSTS; SOLVENTS; EXCHANGE;
D O I
10.1016/j.tetasy.2009.09.015
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The preparation and application of a new series of chiral ionic liquids are described. The salts are based on imidazolinium cations. Some of the cations also incorporated an axial chirality at the C(2) position next to the central chirality. These cations display a very high rotational barrier along the arene-imidazolinium axis. Furthermore. an analogue with a chiral anion was prepared. The salts have low melting points. Their potential as solvents and as chiral shift reagents was explored, resulting for the first time in an example of a chiral ionic liquid as a shift reagent for a neutral compound. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2344 / 2350
页数:7
相关论文
共 50 条
  • [1] Novel imidazolinium ionic liquids and organic salts
    Chong, Alison L.
    Forsyth, Maria
    MacFarlane, Douglas R.
    ELECTROCHIMICA ACTA, 2015, 159 : 219 - 226
  • [2] Thiazolinium salts: New chiral ionic liquids derived from the chiral pool
    Gaumont, AC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U118 - U118
  • [3] Thermochemical and Structural Studies of New Chiral and Achiral Long Alkyl Chain Functionalized Imidazolinium Ionic Liquids
    Seidl, Vera
    Sternberg, Michelle
    Heinemann, Frank W.
    Schmiele, Martin
    Unruh, Tobias
    Wasserscheid, Peter
    Meyer, Karsten
    CRYSTAL GROWTH & DESIGN, 2021, 21 (11) : 6276 - 6288
  • [4] New pyridinium chiral ionic liquids
    Patrascu, C
    Sugisaki, C
    Mingotaud, C
    Marty, JD
    Génisson, Y
    Lauth-de Viguerie, N
    HETEROCYCLES, 2004, 63 (09) : 2033 - 2041
  • [5] Methylated Imidazolinium-Dithiocarboxylates: Two Representatives of a New Class of Ionic Liquids
    Blanrue, Amelie
    Wilhelm, Rene
    SYNTHESIS-STUTTGART, 2009, (04): : 583 - 586
  • [6] Synthesis of new chiral ionic liquids based on (-)-menthol and (-)-borneol
    Matos, Ricardo Alexandre F.
    Andrade, Carlos Kleber Z.
    TETRAHEDRON LETTERS, 2008, 49 (10) : 1652 - 1655
  • [7] Synthesis of novel spiro imidazolium salts as chiral ionic liquids
    Patil, Mahesh L.
    Rao, C. V. Laxman
    Takizawa, Shinobu
    Takenaka, Kazuhiro
    Onitsuka, Kiyotaka
    Sasai, Hiroaki
    TETRAHEDRON, 2007, 63 (51) : 12702 - 12711
  • [8] Chiral ionic liquids based on abietane
    V. A. Glushkov
    M. S. Kotelev
    K. S. Rudovskii
    O. A. Maiorova
    A. V. Tarantin
    A. G. Tolstikov
    Russian Journal of Organic Chemistry, 2009, 45 : 404 - 407
  • [9] Chiral ionic liquids based on abietane
    Glushkov, V. A.
    Kotelev, M. S.
    Rudovskii, K. S.
    Maiorova, O. A.
    Tarantin, A. V.
    Tolstikov, A. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (03) : 404 - 407
  • [10] New Chiral Ionic Liquids Based on Enantiopure Sulfate and Sulfonate Anions for Chiral Recognition
    Winkel, Andreas
    Wilhelm, Rene
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (30) : 5817 - 5824