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  • Arylation of [6,6]-spiroacetal enol ethers: reactivity and rearrangement

    Author(s)
    Aumann, Kylee M
    Healy, Peter C
    Coster, Mark J
    Griffith University Author(s)
    Healy, Peter C.
    Year published
    2011
    Metadata
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    Abstract
    Attempts to selectively arylate [6,6]-spiroacetal enol ethers at the 2-position delivered unexpected results. Palladium-mediated arylation conditions afforded the double-Heck product, whereas reaction with benzenesulfinic acid resulted in a facile rearrangement into the corresponding 5-phenylsulfonyl-3,4,5,6-tetrahydrochromans, providing access to 5-aryl-3,4,5,6-tetrahydrochroman and hexahydrochroman derivatives.Attempts to selectively arylate [6,6]-spiroacetal enol ethers at the 2-position delivered unexpected results. Palladium-mediated arylation conditions afforded the double-Heck product, whereas reaction with benzenesulfinic acid resulted in a facile rearrangement into the corresponding 5-phenylsulfonyl-3,4,5,6-tetrahydrochromans, providing access to 5-aryl-3,4,5,6-tetrahydrochroman and hexahydrochroman derivatives.
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    Journal Title
    Tetrahedron Letters
    Volume
    52
    Issue
    10
    DOI
    https://doi.org/10.1016/j.tetlet.2010.12.076
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Organic chemical synthesis
    Publication URI
    http://hdl.handle.net/10072/42572
    Collection
    • Journal articles

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