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
收藏
页码：8630 / 8635
页数：6
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