Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds

Jonathan R. Powell, Sally Dixon, Mark E. Light, Jeremy Dunbar Kilburn

    Research output: Contribution to journalArticle

    8 Citations (Scopus)

    Abstract

    Samarium(II) diiodide-mediated intramolecular cycloclimerisation of simple bis-enones and -enoates in THF/MeOH has been investigated. Spirocyclic and elaborated polycyclic products, including stereodefined cis-bicyclo[3.3.0]octane and trans-bicyclo[4.3.0]nonanes, are obtained in synthetically useful yield. (C) 2009 Elsevier Ltd. All rights reserved.

    Original languageEnglish
    Pages (from-to)3564-3567
    Number of pages4
    JournalTetrahedron Letters
    Volume50
    Issue number26
    Early online date13 Mar 2009
    DOIs
    Publication statusPublished - 1 Jul 2009

    Keywords

    • ALPHA,BETA-UNSATURATED KETONES
    • REDUCTIVE CYCLIZATION
    • ACID-DERIVATIVES
    • ENONES
    • HYDRODIMERIZATION
    • IODIDE
    • HMPA

    Cite this

    Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds. / Powell, Jonathan R.; Dixon, Sally; Light, Mark E.; Kilburn, Jeremy Dunbar.

    In: Tetrahedron Letters, Vol. 50, No. 26, 01.07.2009, p. 3564-3567.

    Research output: Contribution to journalArticle

    Powell, Jonathan R. ; Dixon, Sally ; Light, Mark E. ; Kilburn, Jeremy Dunbar. / Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 26. pp. 3564-3567.
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    abstract = "Samarium(II) diiodide-mediated intramolecular cycloclimerisation of simple bis-enones and -enoates in THF/MeOH has been investigated. Spirocyclic and elaborated polycyclic products, including stereodefined cis-bicyclo[3.3.0]octane and trans-bicyclo[4.3.0]nonanes, are obtained in synthetically useful yield. (C) 2009 Elsevier Ltd. All rights reserved.",
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    AU - Powell, Jonathan R.

    AU - Dixon, Sally

    AU - Light, Mark E.

    AU - Kilburn, Jeremy Dunbar

    N1 - We thank the EPSRC for a studentship (J.R.P.).

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    KW - ENONES

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