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    Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

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    Issue Date
    2014-07-07
    Author
    Rubina, Marina
    Sherrill, William M.
    Barkov, Alexey Yu
    Rubin, Michael
    Publisher
    Beilstein-Institut
    Type
    Article
    Article Version
    Scholarly/refereed, publisher version
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    Abstract
    A novel class of chiral phosphanyl-oxazoline (PHOX) ligands with a conformationally rigid cyclopropyl backbone was synthesized and tested in the intermolecular asymmetric Heck reaction. Mechanistic modelling and crystallographic studies were used to predict the optimal ligand structure and helped to design a very efficient and highly selective catalytic system. Employment of the optimized ligands in the asymmetric arylation of cyclic olefins allowed for achieving high enantioselectivities and significantly suppressing product isomerization. Factors affecting the selectivity and the rate of the isomerization were identified. It was shown that the nature of this isomerization is different from that demonstrated previously using chiral diphosphine ligands.
    URI
    http://hdl.handle.net/1808/15017
    DOI
    https://doi.org/10.3762/bjoc.10.158
    Collections
    • Chemistry Scholarly Works [610]
    Citation
    Marina Rubina, William M Sherrill, Alexey Yu Barkov, Michael Rubin "Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction" Beilstein J Org Chem. 2014; 10: 1536–1548. Published online 2014 July 7. http://dx.doi.org/10.3762/bjoc.10.158

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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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