The first report of unusual flipping of the cycloadducts from 1,3-dipolar cycloaddition of 3,4,5,6-tetrahydropyridine N-oxide to N-cinnamoyl piperidines
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- 作者：Avijit Banerji ; Debasish Bandyopadhyay ; Piyali Sengupta ; Bidyut Basak ; Thierry Prangé ; and Alain Neuman
- 关键词：Nitrones ; Dipolar cycloaddition ; Intermolecular ; Isoxazolidines
- 刊名：Tetrahedron Letters
- 出版年：2006
- 出版时间：5 June 2006
- 年：2006
- 卷：47
- 期：23
- 页码：3827-3830
- 全文大小：208 K
文摘
A series of cycloadducts possessing unusual flipping modes have been isolated from the 1,3-dipolar cycloaddition of 3,4,5,6-tetrahydropyridine N-oxide to piperidides of cinnamic acid and para-substituted cinnamic acids and these were analyzed by X-ray crystallography to reveal novel solid-state structures. The presence of two different flippomers arising due to flipping of the six/five bicyclic ring was confirmed both in solid state and in solution. This is the first observation of 1,3-dipolar cycloadducts having two different flippomers arising due to flipping of the isoxazolidine ring.