Display Settings:

Format

Send to:

Choose Destination
We are sorry, but NCBI web applications do not support your browser and may not function properly. More information
    J Am Chem Soc. 2006 Apr 12;128(14):4576-7.

    [3,3]-rearrangements of phosphonium ylides.

    Source

    Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

    Abstract

    Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields. This new reaction manifold for phosphorus ylides is tolerant of a range of substitution patterns on the reactants and provides access to structurally complex intermediates for the synthesis of enzyme inhibitors, aminophosphonic acids, and natural products.

    PMID:
    16594686
    [PubMed - indexed for MEDLINE]

    LinkOut - more resources

    Full Text Sources

    Other Literature Sources

    Molecular Biology Databases

      Supplemental Content

      Icon for American Chemical Society

      Save items

      Recent activity

      Your browsing activity is empty.

      Activity recording is turned off.

      Turn recording back on

      See more...
      Write to the Help Desk