Elsevier

Tetrahedron Letters

Volume 47, Issue 23, 5 June 2006, Pages 3827-3830
Tetrahedron Letters

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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Abstract

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.

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Acknowledgements

D.B. thanks UGC, New Delhi, for the award of a fellowship. Thanks are accorded to Professor Sibdas. Ray and Professor (Mrs.) Julie Banerji, Department of Chemistry, Calcutta University, for helpful discussions.

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