Issue 11, 2015

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
09 Jun 2015
Accepted
10 Aug 2015
First published
27 Aug 2015
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2015,2, 1445-1449

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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