New Chiral Ionic Liquids Based on Enantiopure Sulfate and Sulfonate Anions for Chiral Recognition

被引：28
|
作者：
Winkel, Andreas [2 ]
Wilhelm, Rene [1 ,3 ]
机构：
[1] Nicholas Copernicus Univ, Fac Chem, PL-87100 Torun, Poland
[2] Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany
[3] Univ Paderborn, Dept Chem, D-33098 Paderborn, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 30期
关键词：
Ionic liquids; Chirality; Anions; Green chemistry; Chiral recognition; IMIDAZOLINIUM SALTS; AMINO-ACID; DESIGN; CATALYSTS; SOLVENTS;
D O I：
10.1002/ejoc.201000801
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of new chiral ionic liquids with chiral anions is described. Chiral sulfate anions were prepared from alcohols of the "chiral pool" in good yields. Subsequent ion metathesis resulted in new salts with tetrabutylphosphonium and 1-butyl-3-methylimidazolium (BMIM) cations. In addition, the synthesis of chiral sulfonate anions from (R)-phenylethylamine and formaldehyde-sodium hydrogen sulfate, or sodium vinyl sulfonate is shown, giving new Bronsted basic chiral ionic liquids. The potential of the new ionic liquids as chiral shift reagents was explored. It was possible to use, in addition to Mosher's acid and the Bronsted basic ionic liquids, also 2,2,2-trifluoro-1-phenylethanol with the chiral salts. The neutral alcohol was found to interact with the chiral anions by hydrogen bonding.
引用
收藏
页码：5817 / 5824
页数：8
相关论文
共 50 条
  • [1] Straightforward synthesis of chiral sulfonate-based ionic liquids from amino alcohols for chiral recognition
    Feuge, Niklas
    Wilhelm, Rene
    CHIRALITY, 2023, 35 (12) : 993 - 1011
  • [2] Synthesis and phytotoxicity of new ionic liquids incorporating chiral cations and/or chiral anions
    Balczewski, Piotr
    Bachowska, Barbara
    Bialas, Tomasz
    Biczak, Robert
    Wieczorek, Wanda M.
    Balinska, Agnieszka
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (05) : 1881 - 1892
  • [3] Chiral ionic liquids based on nicotine for the chiral recognition of carboxylic acids
    Heckel, Tatjana
    Winkel, Andreas
    Wilhelm, Rene
    TETRAHEDRON-ASYMMETRY, 2013, 24 (18) : 1127 - 1133
  • [4] Synthesis and applications of carbohydrate based chiral ionic liquids as chiral recognition agents and organocatalysts
    Kaur, Nirmaljeet
    Chopra, Harish Kumar
    JOURNAL OF MOLECULAR LIQUIDS, 2020, 298
  • [5] Chiral Recognition Methods in Analytical Chemistry: Role of the Chiral Ionic Liquids
    Singh, Avtar
    Kaur, Nirmaljeet
    Chopra, Harish Kumar
    CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY, 2019, 49 (06) : 553 - 569
  • [6] New cations for ionic liquids, including chiral adjuncts with phosphate and sulfonylimide anions
    Engel, R
    Lall-Ramnarine, SI
    Coleman, D
    Thomas, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U117 - U117
  • [7] New chiral ionic liquids based on imidazolinium salts
    Winkel, Andreas
    Wilhelm, Rene
    TETRAHEDRON-ASYMMETRY, 2009, 20 (20) : 2344 - 2350
  • [8] New Cations for Ionic Liquids, Including Chiral Adjuncts with Phosphate and Sulfonylimide Anions
    Engel, Robert
    Lall-Ramnarine, Sharon
    Coleman, Delroy
    Thomas, Marie
    IONIC LIQUIDS IN ORGANIC SYNTHESIS, 2007, 950 : 259 - 266
  • [9] ANYL 70-Synthesis and properties of a group of chiral ionic liquids with chiral anions
    Yu, Shaofang
    Tran, Chieu D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [10] 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
12345