Pyrrolidine-thioxotetrahydropyrimidinone as an efficient organocatalyst for the enantioselective Michael addition of cyclic ketones to nitrodienes

被引：14

作者：

Tsakos, Michail ^{[1
]}

Trifonidou, Maria ^{[1
]}

Kokotos, Christoforos G. ^{[1
]}

机构：

[1] Univ Athens, Dept Chem, Organ Chem Lab, Athens 15771, Greece

来源：

TETRAHEDRON | 2012年 / 68卷 / 41期

关键词：

Michael addition; Organocatalysis; Nitrodienes; Thioxotetrahydropyrimidinone; Asymmetric synthesis; PRIMARY AMINE-THIOUREAS; CONJUGATE ADDITION; NITROOLEFINS; ALDEHYDES; CYCLOHEXANONE; CONSTRUCTION; DERIVATIVES; CHEMISTRY; CATALYST; PROLINOL;

D O I：

10.1016/j.tet.2012.07.078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Among the various Michael additions, the enantioselective reaction between cyclic ketones and nitrodienes has received little attention in comparison to the corresponding reaction with nitroolefins. A bifunctional organocatalyst consisting of the pyrrolidine moiety and a thioxotetrahydropyrimidinone ring successfully catalyzed this asymmetric transformation. The products of the reaction between various ketones and nitrodienes were obtained in high yields (up to 96%) with excellent diastereo- (up to >98:2 dr) and enantioselectivities (up to 99:1% er). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：8630 / 8635

页数：6

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