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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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Publication details

The article was received on 09 Jun 2015, accepted on 10 Aug 2015 and first published on 27 Aug 2015


Article type: Research Article
DOI: 10.1039/C5QO00183H
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Citation: Org. Chem. Front., 2015,2, 1445-1449
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    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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