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Issue 11, 2015
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γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines

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Abstract

1,3,5-Substituted pyrrolidin-2-ones were synthesised via an iodine mediated cyclisation of 3-methyl substituted homoallylamines in good to excellent yield, as mixtures of diastereoisomers. These were separable and their identity confirmed by techniques including single crystal X-ray diffraction. When 3-phenyl substituted homoallylamines were cyclised intriguing fused tricyclic motifs were obtained as C2-symmetric racemates, whose structures were also confirmed by techniques including single crystal X-ray diffraction analysis.

Graphical abstract: γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines

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Supplementary files

Article information


Submitted
09 Jun 2015
Accepted
10 Aug 2015
First published
27 Aug 2015

This article is Open Access

Org. Chem. Front., 2015,2, 1445-1449
Article type
Research Article
Author version available

γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines

M. A. Hama Salih, L. Male, N. Spencer and J. S. Fossey, Org. Chem. Front., 2015, 2, 1445
DOI: 10.1039/C5QO00183H

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