A remarkable chiral recognition of racemic Mosher's acid salt by naturally derived chiral ionic liquids using 19F NMR spectroscopy

被引:35
作者
Jayachandra, R. [1 ]
Reddy, Sabbasani Rajasekhara [1 ]
机构
[1] VIT Univ, Sch Adv Sci, Div Organ Chem, Vellore 632014, Tamil Nadu, India
关键词
TRANSFER RADICAL POLYMERIZATION; CARBOHYDRATES SYNTHESIS; IMIDAZOLINIUM SALTS; MICHAEL ADDITION; DESIGN; SOLVENTS;
D O I
10.1039/c6ra02792j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new class of D-xylose derived imidazolium-based chiral ionic liquids were designed and synthesized via simple tuning approaches. The developed chiral ionic liquids were tested for their chiral recognition properties with racemic Mosher's acid salt using F-19 NMR spectroscopy. For the first time, we demonstrate the excellent enantioselective discrimination of the racemic salt using significantly less equivalents of carbohydrate derived chiral ionic liquids. We have determined the enantiomeric excess values of non-racemic mixtures of Mosher's acid salts using F-19 NMR spectroscopy.
引用
收藏
页码:39758 / 39761
页数:4
相关论文
共 49 条
[1]   Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].
Baudequin, C ;
Brégeon, D ;
Levillain, J ;
Guillen, F ;
Plaquevent, JC ;
Gaumont, AC .
TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945
[2]   Ionic liquids and chirality: opportunities and challenges [J].
Baudequin, C ;
Baudoux, J ;
Levillain, J ;
Cahard, D ;
Gaumont, AC ;
Plaquevent, JC .
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093
[3]   Radical polymerization in a chiral ionic liquid: Atom transfer radical polymerization of acrylates [J].
Biedron, T ;
Kubisa, P .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2005, 43 (15) :3454-3459
[4]   Ionic liquids as reaction media for polymerization processes: atom transfer radical polymerization (ATRP) of acrylates in ionic liquids [J].
Biedron, T ;
Kubisa, P .
POLYMER INTERNATIONAL, 2003, 52 (10) :1584-1588
[5]   Advances in chiral ionic liquids derived from natural amino acids [J].
Chen, Xuewei ;
Li, Xuehui ;
Hu, Aixi ;
Wang, Furong .
TETRAHEDRON-ASYMMETRY, 2008, 19 (01) :1-14
[6]   Design and synthesis of imidazolinium salts derived from (L)-valine. Investigation of their potential in chiral molecular recognition [J].
Clavier, H ;
Boulanger, L ;
Audic, N ;
Toupet, L ;
Mauduit, M ;
Guillemin, JC .
CHEMICAL COMMUNICATIONS, 2004, (10) :1224-1225
[7]   Chiral ionic liquids: Synthesis and applications [J].
Ding, J ;
Armstrong, DW .
CHIRALITY, 2005, 17 (05) :281-292
[8]   Use of chiral ionic liquids as solvents for the enantioselective photoisomerization of dibenzobicyclo[2.2.2]octatrienes [J].
Ding, J ;
Desikan, V ;
Han, XX ;
Xiao, TL ;
Ding, RF ;
Jenks, WS ;
Armstrong, DW .
ORGANIC LETTERS, 2005, 7 (02) :335-337
[9]   Chiral ionic liquids as stationary phases in gas chromatography [J].
Ding, J ;
Welton, T ;
Armstrong, DW .
ANALYTICAL CHEMISTRY, 2004, 76 (22) :6819-6822
[10]   Synthesis, Biological Activity, and Molecular Modeling Studies of 1H-1,2,3-Triazole Derivatives of Carbohydrates as α-Glucosidases Inhibitors [J].
Ferreira, Sabrina B. ;
Sodero, Ana C. R. ;
Cardoso, Mariana F. C. ;
Lima, Emerson S. ;
Kaiser, Carlos R. ;
Silva, Floriano P., Jr. ;
Ferreira, Vitor F. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (06) :2364-2375