New chiral imidazolinic derivatives

被引:46
作者
Génisson, Y
Lauth-de Viguerie, N
André, C
Baltas, M
Gorrichon, L
机构
[1] Univ Toulouse 3, CNRS, UMR 5068, SPCMIB, F-31062 Toulouse, France
[2] Univ Toulouse 3, CNRS, UMR 5623, IMRCP, F-31062 Toulouse, France
关键词
D O I
10.1016/j.tetasy.2005.01.014
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel C-2 substituted 4,5-dihydroimidazoles and imidazoles bearing an N-linked stereogenic group were rapidly prepared from a chiral primary amine. Quaternization of these derivatives resulted in a range of scalemic room temperature ionic liquids. The ability of the imidazolium species to act as reaction medium and/or phase transfer catalyst was also assessed. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1017 / 1023
页数:7
相关论文
共 30 条
[1]   Synthesis of chiral ionic liquids from natural amino acids [J].
Bao, WL ;
Wang, ZM ;
Li, YX .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :591-593
[2]  
BARCO A, 1977, SYNTHESIS-STUTTGART, P837
[3]   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
[4]   Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction [J].
Dere, RT ;
Pal, RR ;
Patil, PS ;
Salunkhe, MM .
TETRAHEDRON LETTERS, 2003, 44 (28) :5351-5353
[5]   On the solid, liquid and solution structural organization of imidazolium ionic liquids [J].
Dupont, J .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2004, 15 (03) :341-350
[6]   Diels-Alder reactions in ionic liquids - A safe recyclable alternative to lithium perchlorate-diethyl ether mixtures [J].
Earle, MJ ;
McCormac, PB ;
Seddon, KR .
GREEN CHEMISTRY, 1999, 1 (01) :23-25
[7]  
FIROUZABADI H, 1978, TETRAHEDRON LETT, P839
[8]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[9]   Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].
France, S ;
Guerin, DJ ;
Miller, SJ ;
Lectka, T .
CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012
[10]   Synthesis of substituted imidazoles via organocatalysis [J].
Frantz, DE ;
Morency, L ;
Soheili, A ;
Murry, JA ;
Grabowski, EJJ ;
Tillyer, RD .
ORGANIC LETTERS, 2004, 6 (05) :843-846