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
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