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 Qas 2015
Accepted
10 Leq 2015
First published
27 Leq 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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements