Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles

被引：188

作者：

Gogoi, Sanjib ^{[1
]}

Zhao, Cong-Gui ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 19期

关键词：

Dihydropyrano[2,3-c]pyrazole; Pyrazole; Dihydropyrane; Cinchona alkaloid; Organocatalysis; Multi-component reaction; Tandem reaction; MICHAEL-HENRY REACTION; MULTICOMPONENT REACTIONS; DOMINO REACTIONS; MULTISUBSTITUTED CYCLOPENTANES; NONADJACENT STEREOCENTERS; MOLLUSCICIDAL ACTIVITY; ASYMMETRIC-SYNTHESIS; DERIVATIVES; CATALYSIS; CASCADE;

D O I：

10.1016/j.tetlet.2009.02.210

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

The first enantioselective synthesis of biologically active 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles has been achieved through a cinchona alkaloid-catalyzed tandem Michael addition and Thorpe-Ziegler type reaction between 2-pyrazolin-5-ones and benzylidenemalononitriles. The reaction may also be carried out in a three-component or a four-component fashion via the in situ formation of these two components from simple and readily available starting materials. The desired products were obtained in excellent yields with mediocre to excellent enantioselectivities (up to >99% ee). (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2252 / 2255

页数：4

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