Samarium(II)-mediated reactions of γ,δ-unsaturated ketones. Cyclization and fragmentation processes

Thomas K. Hutton, Kenneth Muir, David J. Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    (Matrix Presented) On treatment with samarium(II) iodide, γ,δ-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.
    Original languageEnglish
    Pages (from-to)2345-2347
    Number of pages2
    JournalOrganic Letters
    Volume4
    Issue number14
    DOIs
    Publication statusPublished - 11 Jul 2002

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