Immobilization of catalysts derived from Cinchona alkaloids on modified poly(ethylene glycol)

被引：72
作者：
Danelli, T
Annunziata, R
Benaglia, M
Cinquini, M
Cozzi, F
Tocco, G
机构：
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] Univ Milan, CNR, ISTM, I-20133 Milan, Italy
[3] Univ Milan, CISI, Ctr Eccellenza, I-20133 Milan, Italy
[4] Univ Cagliari, Dipartimento Farmaco Chim Tecnol, I-09124 Cagliari, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 04期
关键词：
D O I：
10.1016/S0957-4166(02)00830-3
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The straightforward immobilization of some derivatives of Cinchona alkaloids on modified poly(ethylene glycol)s is reported. The compounds. obtained by simple reactions exploiting different sites for the attachment of the alkaloids to the polymer, were tested as catalysts in the enantioselective benzylation of the benzophenone imine of glycine t-butyl ester (ee Lip to 64%) and in the conjugate addition of thiophenol to cyclohexenone (ee 22%). The observed stereoselectivities were compared to those obtained either with the unsupported catalysts or with the catalysts immobilized on different polymeric matrixes. The influence of the poly(ethylene glycol) moieties on the catalytic activity is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：461 / 467
页数：7
相关论文
共 34 条
[21]  
Kacprzak K, 2001, SYNTHESIS-STUTTGART, P961
[22]   A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of alpha-amino acids [J].
Lygo, B ;
Wainwright, PG .
TETRAHEDRON LETTERS, 1997, 38 (49) :8595-8598
[23]   Structure-selectivity studies on catalysts for the phase-transfer catalysed asymmetric alkylation of glycine imine esters [J].
Lygo, B ;
Crosby, J ;
Lowdon, TR ;
Wainwright, PG .
TETRAHEDRON, 2001, 57 (12) :2391-2402
[24]  
Mohar B, 2001, ANGEW CHEM INT EDIT, V40, P4214, DOI 10.1002/1521-3773(20011119)40:22<4214::AID-ANIE4214>3.0.CO
[25]  
2-B
[26]   A MILD AND EFFICIENT ROUTE TO SCHIFF-BASE DERIVATIVES OF AMINO-ACIDS [J].
ODONNELL, MJ ;
POLT, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2663-2666
[27]  
Salvadori P, 1999, SYNLETT, P1181
[28]   Enantioselective fluorination mediated by cinchona alkaloid derivatives/selectfluor combinations:: Reaction scope and structural information for N-fluorocinchona alkaloids [J].
Shibata, N ;
Suzuki, E ;
Asahi, T ;
Shiro, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (29) :7001-7009
[29]   PARTIAL SYNTHESIS OF 6'-HYDROXYCINCHONINE AND ITS ANTI-ARRHYTHMIC ACTIVITY IN MICE [J].
SMALL, LD ;
ROSENBERG, H ;
NWANGWU, PU ;
HOLCSLAW, TL ;
STOHS, SJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (08) :1014-1016
[30]   The development of the first catalyzed reaction of ketenes and imines:: Catalytic, asymmetric synthesis of β-lactams [J].
Taggi, AE ;
Hafez, AM ;
Wack, H ;
Young, B ;
Ferraris, D ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6626-6635
1234