Asymmetric organocatalytic Henry reaction

被引:300
作者
Marcelli, T [1 ]
van der Haas, RNS [1 ]
van Maarseveen, JH [1 ]
Hiemstra, H [1 ]
机构
[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands
关键词
alkaloids; asymmetric catalysis; Henry reaction; hydrogen bonds; organocatalysis;
D O I
10.1002/anie.200503724
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The nitroaldol (Henry) reaction between aromatic aldehydes and nitromethane can be carried out in high yields and enantiomeric excess by using a novel Cinchona-derived thiourea catalyst. Hydrogen-bond donors at the C6′ position in these organocatalysts are shown to induce preferential formation of one enantiomer. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:929 / 931
页数:3
相关论文
共 48 条
[41]  
2-V
[42]   Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine [J].
Trost, BM ;
Yeh, VSC ;
Ito, H ;
Bremeyer, N .
ORGANIC LETTERS, 2002, 4 (16) :2621-2623
[43]   Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts [J].
Vakulya, B ;
Varga, S ;
Csámpai, A ;
Soós, T .
ORGANIC LETTERS, 2005, 7 (10) :1967-1969
[44]   Metal-free, noncovalent catalysis of Diels-Alder reactions by neutral hydrogen bond donors in organic solvents and in water [J].
Wittkopp, A ;
Schreiner, PR .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (02) :407-414
[45]  
XU X, 2005, IN PRESS CHEM EUR J
[46]   Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives [J].
Ye, JX ;
Dixon, DJ ;
Hynes, PS .
CHEMICAL COMMUNICATIONS, 2005, (35) :4481-4483
[47]  
Yoon T.P., 2005, Angew. Chem, V117, P470, DOI [DOI 10.1002/ANGE.200461814, 10.1002/ange.200461814]
[48]   Highly enantioselective thiourea-catalyzed nitro-Mannich reactions [J].
Yoon, TP ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :466-468