Design and synthesis of imidazolinium salts derived from (L)-valine. Investigation of their potential in chiral molecular recognition

被引：116

作者：

Clavier, H

Boulanger, L

Audic, N

Toupet, L

Mauduit, M ^{[1
]}

Guillemin, JC

机构：

[1] Ecole Natl Super Chim Rennes, Inst Chim Rennes, CNRS, UMR 6052, F-35700 Rennes, France

[2] Univ Rennes 1, CNRS, UMR 6626, F-35700 Rennes, France

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 10期

关键词：

D O I：

10.1039/b402368d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several imidazolinium salts are synthesized from (L)-valine. A study of the structure relationships is achieved to obtain high diastereomeric interactions with an anionic substrate. High splitting up to 60 Hz of the (rac)-potassium Mosher's salt are observed by NMR spectroscopy.

引用

收藏

页码：1224 / 1225

页数：2

相关论文

共 18 条

[1]

Anastas P. T., 1999, GREEN CHEM FRONTIERS

[2] 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

[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] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

[5]

Dupont J, 2000, CHEM-EUR J, V6, P2377, DOI 10.1002/1521-3765(20000703)6:13<2377::AID-CHEM2377>3.3.CO

[6]

2-C

[7] ASYMMETRIC INDUCTION IN THE BAYLIS-HILLMAN REACTION [J].

GILBERT, A ;

HERITAGE, TW ;

ISAACS, NS .

TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :969-972

[8] Design and synthesis of a novel imidazolium-based ionic liquid with planar chirality [J].

Ishida, Y ;

Miyauchi, H ;

Saigo, K .

CHEMICAL COMMUNICATIONS, 2002, (19) :2240-2241

[9] Convenient syntheses of unsymmetrical imidazolidines [J].

Katritzky, AR ;

Suzuki, K ;

He, HY .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3109-3114

[10] Synthesis and properties of thiazoline based ionic liquids derived from the chiral pool [J].

Levillain, J ;

Dubant, G ;

Abrunhosa, I ;

Gulea, M ;

Gaumont, AC .

CHEMICAL COMMUNICATIONS, 2003, (23) :2914-2915