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    Mechanistic origin of the stereodivergence in decarboxylative allylation

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    Chattopadhyay_2010.pdf (1.096Mb)
    Issue Date
    2010-07-02
    Author
    Chattopadhyay, Kalicharan
    Jana, Ranjan
    Day, Victor W.
    Douglas, Justin T.
    Tunge, Jon A.
    Publisher
    American Chemical Society
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
    Rights
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol101042x.
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    Abstract
    A stereochemical test has been used to probe the mechanism of decarboxylative allylation. This probe suggests that the mechanism of DcA reactions can change based on the substitution pattern at the α-carbon of the nucleophile, however reaction via stabilized malonate nucleophiles is the lower energy pathway. Lastly, this mechanistic proposal has predictive power and can be used to explain chemoselectivities in decarboxylative reactions that were previously confounding.
    URI
    http://hdl.handle.net/1808/23475
    DOI
    https://doi.org/10.1021/ol101042x
    Collections
    • Chemistry Scholarly Works [626]
    Citation
    Chattopadhyay, K., Jana, R., Day, V. W., Douglas, J. T., & Tunge, J. A. (2010). Mechanistic origin of the stereodivergence in decarboxylative allylation. Organic Letters, 12(13), 3042–3045. http://doi.org/10.1021/ol101042x

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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