An improved protocol for the direct asymmetric aldol reaction in ionic liquids, catalysed by onium ion-tagged prolines

被引：99
作者：
Lombardo, Marco
Pasi, Filippo
Easwar, Srinivasan
Trombini, Claudio
机构：
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Consorzio Interuniv Nazl La Chim Ambiente, I-30175 Marghera, VE, Italy
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 11-12期
关键词：
aldol reaction; ionic liquids; organocatalysis; proline-derived catalysis;
D O I：
10.1002/adsc.200700136
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Two onium ion-tagged prolines, imidazolium bis(trifluoromethylsulfonyl)imide-substituted proline 6 and butyldimethylammonium bis(trifluoromethylsulfonyl)imide-substituted proline 7, were synthesised and their catalytic activity in the direct asymmetric aldol condensation was studied in ionic liquids. For the reaction of acetone with various aldehydes, using 5% of the catalyst, the yields of the aldols varied between 50-85% while the ee values were in the 80-85% range. Other ketones were studied too, the yields obtained in those cases being in the 35-78% range while the enantioselectivities varied between 75-94%.
引用
收藏
页码：2061 / 2065
页数：5
相关论文
共 21 条
[1]  
Chowdari NS, 2003, SYNLETT, P1906
[2]   Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides [J].
Cordova, Armando ;
Zou, Weibiao ;
Dziedzic, Pawel ;
Ibrahem, Ismail ;
Reyes, Efraim ;
Xu, Yongmei .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) :5383-5397
[3]   TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].
EDER, U ;
SAUER, G ;
WEICHERT, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&
[4]   Supported ionic liquids. New recyclable materials for the L-proline-catalyzed aldol reaction [J].
Gruttadauria, M ;
Riela, S ;
Aprile, C ;
Lo Meo, P ;
D'Anna, F ;
Noto, R .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :82-92
[5]   Supported ionic liquid asymmetric catalysis. A new method for chiral catalysts recycling. The case of proline-catalyzed aldol reaction [J].
Gruttadauria, M ;
Riela, S ;
Lo Meo, P ;
D'Anna, F ;
Noto, R .
TETRAHEDRON LETTERS, 2004, 45 (32) :6113-6116
[6]  
GRUTTADAURIA M, 2006, TETRAHEDRON LETT, V348, P82
[7]   ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].
HAJOS, ZG ;
PARRISH, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621
[8]   Proline-catalysed asymmetric aldol reaction in the room temperature ionic liquid [bmim]PF6 [J].
Kotrusz, P ;
Kmentová, I ;
Gotov, B ;
Toma, S ;
Solcániová, E .
CHEMICAL COMMUNICATIONS, 2002, (21) :2510-2511
[9]   Proline-catalyzed direct asymmetric aldol reactions [J].
List, B ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396
[10]   The ying and yang of asymmetric aminocatalysis [J].
List, B .
CHEMICAL COMMUNICATIONS, 2006, (08) :819-824
123