Synthesis of novel chiral Schiff-base ligands and their application in asymmetric nitro aldol (Henry) reaction

被引:58
作者
Colak, Mehmet [1 ]
Aral, Tarik [1 ]
Hosgoeren, Halil [1 ]
Demirel, Nadir [1 ]
机构
[1] Univ Dicle, Fac Sci, Dept Chem, TR-21280 Diyarbakir, Turkey
关键词
D O I
10.1016/j.tetasy.2007.04.025
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral Schiff-bases prepared from chiral amino alcohols catalyze the enantio selective Henry (nitro aldol) reaction between nitromethane and p-nitrobenzaldehyde in the presence of Cu(OTf)(2) and Zn(OTf)(2). Zn(OTf)(2) promoted the reaction yield, while Cu(OTf)(2) promoted the enantiomeric excess. The highest enantioselectivities were observed with ligand 3 (44% ee) and ligand 5 (47% ee). (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1129 / 1133
页数:5
相关论文
共 38 条
[1]   Self-assembly of heterobimetallic complexes and reactive nucleophiles: A general strategy for the activation of asymmetric reactions promoted by heterobimetallic catalysts [J].
Arai, T ;
Yamada, YMA ;
Yamamoto, N ;
Sasai, H ;
Shibasaki, M .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (11) :1368-1372
[3]   ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION [J].
ARATANI, T ;
YONEYOSHI, Y ;
NAGASE, T .
TETRAHEDRON LETTERS, 1982, 23 (06) :685-688
[4]   Catalytic asymmetric Henry reaction [J].
Boruwa, Joshodeep ;
Gogoi, Naminita ;
Saikia, Partha Pratim ;
Barua, Nabin C. .
TETRAHEDRON-ASYMMETRY, 2006, 17 (24) :3315-3326
[5]   Binuclear versus mononuclear copper complexes as catalysts for asymmetric cyclopropanation of styrene [J].
Cai, LS ;
Mahmoud, H ;
Han, Y .
TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :411-427
[6]   Copper-catalyzed enantioselective Henry reactions of α-keto esters:: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters [J].
Christensen, C ;
Juhl, K ;
Hazell, RG ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4875-4881
[7]   Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters [J].
Christensen, C ;
Juhl, K ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2001, (21) :2222-2223
[8]  
Corey EJ, 1999, ANGEW CHEM INT EDIT, V38, P1931, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO
[9]  
2-4
[10]  
Dossetter AG, 1999, ANGEW CHEM INT EDIT, V38, P2398, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2398::AID-ANIE2398>3.0.CO