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    Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

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    Type
    Article
    Authors
    Zhu, Bo
    Zhang, Wen
    Lee, Richmond
    Han, Zhiqiang
    Yang, Wenguo
    Tan, Davin
    Huang, Kuo-Wei cc
    Jiang, Zhiyong
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2013-05-03
    Online Publication Date
    2013-05-03
    Print Publication Date
    2013-06-24
    Permanent link to this record
    http://hdl.handle.net/10754/562755
    
    Metadata
    Show full item record
    Abstract
    6 in 1: The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E-configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3-hydroxy-2-oxindole derivatives (e.g., CPC-1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π-π* and H-bonding interactions in the transition state. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Citation
    Zhu, B., Zhang, W., Lee, R., Han, Z., Yang, W., Tan, D., … Jiang, Z. (2013). Direct Asymmetric Vinylogous Aldol Reaction of Allyl Ketones with Isatins: Divergent Synthesis of 3-Hydroxy-2-Oxindole Derivatives. Angewandte Chemie International Edition, 52(26), 6666–6670. doi:10.1002/anie.201302274
    Sponsors
    This work was supported by the NSFC (21072044) and the Program for New Century Excellent Talents in University of the Ministry of Education (NCET-11-0938) to Z.J. and by KAUST to K.-W.H.
    Publisher
    Wiley
    Journal
    Angewandte Chemie - International Edition
    DOI
    10.1002/anie.201302274
    PubMed ID
    23650192
    Relations
    Is Supplemented By:
    • [Dataset]
      Zhu, B., Zhang, W., Lee, R., Han, Z., Yang, W., Tan, D., … Jiang, Z. (2013). CCDC 881668: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccylfxv. DOI: 10.5517/ccylfxv HANDLE: 10754/624715
    ae974a485f413a2113503eed53cd6c53
    10.1002/anie.201302274
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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