Enantioselective organocatalytic reactions of 4-hydroxycoumarin and 4-hydroxypyrone with α,β-unsaturated aldehydes -: An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones

被引：84
作者：
Rueping, Magnus [1 ]
Merino, Estibaliz [1 ]
Sugiono, Erli [1 ]
机构：
[1] Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 13期
关键词：
bronsted acids; diarylprolinol ethers; domino reaction; iminium catalysis; pyranocoumarins;
D O I：
10.1002/adsc.200800340
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient, organocatalytic enantioselective addition-cyclization reaction of cyclic 1,3-dicarbonyl compounds with different alpha,beta-unsaturated aldehydes has been developed. The diarylprolinol ether-catalyzed reaction cascade provides a variety of chromenones, quinolinones and pyranones in good yields and with excellent enantioselectivities.
引用
收藏
页码：2127 / 2131
页数：5
相关论文
共 68 条
[51]   A highly enantioselective Bronsted acid catalyzed reaction cascade [J].
Rueping, Magnus ;
Antonchick, Andrey P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (31) :5836-5838
[52]   Asymmetric organocatalysis: An efficient enantioselective access to benzopyranes and chromenes [J].
Rueping, Magnus ;
Sugiono, Erli ;
Merino, Estibaliz .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (21) :6329-6332
[53]   Asymmetric iminium ion catalysis:: An efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones [J].
Rueping, Magnus ;
Sugiono, Erli ;
Merino, Estibaliz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3046-3049
[54]   Organocatalytic enantioselective reduction of Pyridines [J].
Rueping, Magnus ;
Antonchick, Andrey P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4562-4565
[55]   Cooperative coexistence: Effective interplay of two Bronsted acids in the asymmetric synthesis of isoquinuclidines [J].
Rueping, Magnus ;
Azap, Cengiz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7832-7835
[56]   A highly enantioselective bronsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids [J].
Rueping, Magnus ;
Antonchick, Andrey R. ;
Theissmann, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (22) :3683-3686
[57]   Metal-free Bronsted acid catalyzed transfer hydrogenation - New organocatalytic reduction of quinolines [J].
Rueping, Magnus ;
Theissmann, Thomas ;
Antonchick, Andrey P. .
SYNLETT, 2006, (07) :1071-1074
[58]  
Vesely J., 2007, ANGEW CHEM, V119, P792
[59]   Organocatalytic enantioselective aziridination of α,β-unsaturated aldehydes [J].
Vesely, Jan ;
Ibrahem, Ismail ;
Zhao, Gui-Ling ;
Rios, Ramon ;
Cordova, Armando .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (05) :778-781
[60]   An enantioselective organocatalytic oxidative dearomatization strategy [J].
Vo, Ngoc T. ;
Pace, Robert D. M. ;
O'Hara, Fionn ;
Gaunt, Matthew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :404-+
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