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  • A Convenient Triisobutylaluminium (TIBAL)-Promoted Johnson-Claisen Approach to γ,δ-Unsaturated Alcohols

    Author(s)
    L. Cosgrove, Kelly
    P. McGeary, Ross
    Griffith University Author(s)
    Cosgrove, Kelly
    Year published
    2009
    Metadata
    Show full item record
    Abstract
    Mixed ortho esters derived from allylic alcohols undergo methanol elimination in the presence of triisobutylaluminium (TIBAL) at room temperature to form mixed ketene acetals. TIBAL then promotes immediate Claisen rearrangement of these intermediates, and subsequent reduction of the ester products, to give unsaturated ?,d-primary alcohols in a convenient, one-pot procedure.Mixed ortho esters derived from allylic alcohols undergo methanol elimination in the presence of triisobutylaluminium (TIBAL) at room temperature to form mixed ketene acetals. TIBAL then promotes immediate Claisen rearrangement of these intermediates, and subsequent reduction of the ester products, to give unsaturated ?,d-primary alcohols in a convenient, one-pot procedure.
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    Journal Title
    Synlett
    Volume
    2009
    Issue
    11
    DOI
    https://doi.org/10.1055/s-0029-1217382
    Subject
    Organic Chemical Synthesis
    Medicinal and Biomolecular Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/40559
    Collection
    • Journal articles

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