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    N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides

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    acs2Ejoc2E5b01845.pdf
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    Type
    Article
    Authors
    Guo, Hao
    Xing, Fen
    Du, Guang-Fen
    Huang, Kuo-Wei cc
    Dai, Bin
    He, Lin
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2015-11-30
    Online Publication Date
    2015-11-30
    Print Publication Date
    2015-12-18
    Permanent link to this record
    http://hdl.handle.net/10754/582931
    
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    Abstract
    An efficient N-heterocyclic carbene (NHC)-catalysed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol% of the NHC catalyst, both γ-alkyl and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Brønsted base to promote the conjugate addition.
    Citation
    N-Heterocyclic Carbene-Catalysed Diastereoselective Vinylogous Michael Addition Reaction of gamma-Substituted deconjugated Butenolides 2015 The Journal of Organic Chemistry
    Publisher
    American Chemical Society (ACS)
    Journal
    The Journal of Organic Chemistry
    DOI
    10.1021/acs.joc.5b01845
    PubMed ID
    26569552
    Additional Links
    http://pubs.acs.org/doi/10.1021/acs.joc.5b01845
    Relations
    Is Supplemented By:
    • [Dataset]
      Guo, H., Xing, F., Du, G.-F., Huang, K.-W., Dai, B., & He, L. (2016). CCDC 1433704: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1k3wj2. DOI: 10.5517/cc1k3wj2 HANDLE: 10754/624479
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.joc.5b01845
    Scopus Count
    Collections
    Articles; Biological and Environmental Science and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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