Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements

Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadduct...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2003-08, Vol.1 (15), p.2689-2698
Main Authors: Roussel, Christophe, Fihi, Rachid, Ciamala, Kabula, Vebrel, Joël, Zair, Touria, Riche, Claude
Format: Article
Language:English
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Summary:Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadducts in acidic and alkaline media led to different, unexpected and novel rearrangements.
ISSN:1477-0520
1477-0539
DOI:10.1039/b300628j