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    Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides

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    Authors
    Hodgson, David M.
    Glen, Rebecca
    Grant, Guy H.
    Redgrave, Alison J.
    Affiliation
    University of Oxford
    GlaxoSmithKline Medicines Research Centre
    Issue Date
    2003
    
    Metadata
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    Abstract
    An evaluation of α-aryl-α-diazodiones in tandem carbonyl ylide formation−enantioselective [3 + 2]-cycloaddition reactions is described. Such substrates were designed to allow investigation of the electronic characteristics of the dipole upon asymmetric induction. Intramolecular cycloadditions (with a tethered alkene dipolarophile) were found to occur in good to quantitative yields, with a difference in ee exhibited by the two electronically different diazodiones 8 and 9. Intermolecular cycloadditions using diazodiones 12 and 13 with DMAD and arylacetylenes 16−18 again demonstrated that electronics play a key role in determining the outcome of the cycloaddition reactions. Enantioselectivities of up to 76% were observed.
    Citation
    Hodgson, D.M., Glen, R., Grant, G.H. and Redgrave, A.J. (2003) 'Catalytic Enantioselective [3 + 2]-Cycloadditions of Diazoketone-Derived Aryl-Substituted Carbonyl Ylides', The Journal of Organic Chemistry, 68(2), pp.581-586
    Publisher
    American Chemical Society
    Journal
    The Journal of Organic Chemistry
    URI
    http://hdl.handle.net/10547/302107
    DOI
    10.1021/jo026307t
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/jo026307t
    Type
    Article
    Language
    en
    ISSN
    0022-3263
    1520-6904
    ae974a485f413a2113503eed53cd6c53
    10.1021/jo026307t
    Scopus Count
    Collections
    Cell and Cryobiology Research Group

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