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  • Synthesis of Butenolides via a Horner-Wadsworth-Emmons Cascading Dimerization Reaction

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    Everson269069Accepted.pdf (533.4Kb)
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    Accepted Manuscript (AM)
    Author(s)
    Everson, Jack
    Kiefel, Milton J
    Griffith University Author(s)
    Kiefel, Milton
    Year published
    2019
    Metadata
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    Abstract
    The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner–Wadsworth–Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes furnished butenolides, resulting from the dimerization of the HWE product during desilylation of the initially formed HWE adduct. In addition to isolating butenolides in a high yield, we have also determined precisely when dimerization occurs.The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner–Wadsworth–Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes furnished butenolides, resulting from the dimerization of the HWE product during desilylation of the initially formed HWE adduct. In addition to isolating butenolides in a high yield, we have also determined precisely when dimerization occurs.
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    Journal Title
    Journal of Organic Chemistry
    Volume
    84
    Issue
    23
    DOI
    https://doi.org/10.1021/acs.joc.9b02015
    Copyright Statement
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright 2019 American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b02015
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Science & Technology
    Physical Sciences
    Chemistry, Organic
    Chemistry
    LEGIONAMINIC ACID
    Publication URI
    http://hdl.handle.net/10072/392532
    Collection
    • Journal articles

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