Microwave solvent-free synthesis of nitrocyclohexanols

被引：23

作者：

Correc, O

Guillou, K

Hamelin, J

Paquin, L

Texier-Boullet, F

Toupet, L

机构：

[1] CNRS, UMR 6510, F-35042 Rennes, France

[2] Univ Rennes 1, F-35042 Rennes, France

[3] Univ Rennes 1, Grp Mat Condensee & Mat, UMR C66 26, F-35042 Rennes, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 02期

关键词：

nitrocyclohexanols; alpha; beta-enones; Michael additions; alumina-potassium fluoride; solvent-free reactions; microwave activation;

D O I：

10.1016/j.tetlet.2003.10.148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New nitrocyclohexanols 3a-f are synthesized by a clean and original method from nitromethane 1 and unsaturated ketones 2a-f in the presence of solid potassium fluoride-alumina under solvent-free conditions coupled with microwave irradiation. The reaction involves a double and diastereoselective Michael addition followed by ring closure. Another diastereomer 3', which differs by the configuration of C-4, is obtained in the presence of piperidine and EtOH at room temperature. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：391 / 395

页数：5

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