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    Rapid decarboxylative allylation of nitroalkanes

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    Grenning_2010.pdf (921.5Kb)
    Issue Date
    2010-02-19
    Author
    Grenning, Alexander J.
    Tunge, Jon A.
    Publisher
    American Chemical Society
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
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    Abstract
    Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because O-allylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, the preparation of substrate allyl nitroacetates by tandem Knoevenagel/Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.
    URI
    http://hdl.handle.net/1808/23485
    DOI
    https://doi.org/10.1021/ol902828p
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    • Chemistry Scholarly Works [626]
    Citation
    Grenning, A. J., & Tunge, J. A. (2010). Rapid decarboxylative allylation of nitroalkanes. Organic Letters, 12(4), 740. http://doi.org/10.1021/ol902828p

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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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