Combined organo- and gold-catalyzed enantioselective synthesis of bicyclic enones

被引：25

作者：

Zweifel, Theo ^{[1
]}

Hollmann, Dirk ^{[1
]}

Pruger, Birgit ^{[1
]}

Nielsen, Martin ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Ctr Catalysis, Dept Chem, DK-8000 Aarhus C, Denmark

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 11-12期

基金：

瑞士国家科学基金会;

关键词：

TRANSITION-METAL CATALYSIS; PHASE-TRANSFER CATALYST; ALPHA; BETA-UNSATURATED KETONES; CASCADE CATALYSIS; MICHAEL ADDITION; MULTISUBSTITUTED CYCLOPENTANES; SEQUENTIAL HYDROFORMYLATION; ASYMMETRIC ORGANOCATALYSIS; COOPERATIVE CATALYSIS; ALLYLIC ALKYLATION;

D O I：

10.1016/j.tetasy.2010.05.044

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

By combining organocatalysis with gold catalysis highly enantioenriched bicyclic enones are available via an operationally simple one-pot procedure. Iminium-ion activation by cinchona alkaloid-derived primary amine catalysts induces the Michael addition of propargylated malononitriles and cyanoacetates to alpha,beta-unsaturated ketones. The resulting intermediates undergo an exo-dig cyclization, forming a new C-C bond followed by double-bond isomerization to give highly functionalized bicyclic enones in good yields and high enantioselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1624 / 1629

页数：6

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