Supported ionic liquid asymmetric catalysis. A new method for chiral catalysts recycling. The case of proline-catalyzed aldol reaction

被引:120
作者
Gruttadauria, M [1 ]
Riela, S [1 ]
Lo Meo, P [1 ]
D'Anna, F [1 ]
Noto, R [1 ]
机构
[1] Univ Palermo, Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy
关键词
Aldols; silica gel; supported reagents;
D O I
10.1016/j.tetlet.2004.06.066
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for chiral catalysts recycling, based on the supported ionic liquid asymmetric catalysis concept, has been developed. This concept involves the treatment of a monolayer of covalently attached ionic liquid on the surface of silica gel with additional ionic liquid. These layers serve as the reaction phase in which the homogeneous chiral catalyst is dissolved. As first application of this concept the L-proline-catalyzed aldol reaction has been carried out. Good yields and ee values, comparable with those obtained under homogeneous conditions have been obtained. Moreover, this material shows high regenerability. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6113 / 6116
页数:4
相关论文
共 31 条
[1]  
Benaglia M, 2002, ADV SYNTH CATAL, V344, P533, DOI 10.1002/1615-4169(200207)344:5<533::AID-ADSC533>3.0.CO
[2]  
2-Y
[3]   Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].
Bogevig, A ;
Sundén, H ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1109-1112
[4]  
Bogevig A, 2003, SYNLETT, P1915
[5]  
Chowdari NS, 2003, SYNLETT, P1906
[6]   Proline-catalyzed asymmetric assembly reactions:: enzyme-like assembly of carbohydrates and polyketides from three aldehyde substrates [J].
Chowdari, NS ;
Ramachary, DB ;
Córdova, A ;
Barbas, CF .
TETRAHEDRON LETTERS, 2002, 43 (52) :9591-9595
[7]   Direct catalytic asymmetric cross-aldol reactions in ionic liquid media [J].
Córdova, A .
TETRAHEDRON LETTERS, 2004, 45 (20) :3949-3952
[9]   Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :301-303
[10]   A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].
Córdova, A ;
Notz, W ;
Zhong, GF ;
Betancort, JM ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843