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    Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water

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    Type
    Article
    Authors
    Zhu, Bo
    Yan, Lin
    Pan, Yuanhang
    Lee, Richmond
    Liu, Hongjun
    Han, Zhiqiang
    Huang, Kuo-Wei cc
    Tan, Choonhong
    Jiang, Zhiyong
    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
    2011-08-19
    Permanent link to this record
    http://hdl.handle.net/10754/561844
    
    Metadata
    Show full item record
    Abstract
    A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments. © 2011 American Chemical Society.
    Citation
    Zhu, B., Yan, L., Pan, Y., Lee, R., Liu, H., Han, Z., … Jiang, Z. (2011). Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita–Baylis–Hillman Carbonates with Water. The Journal of Organic Chemistry, 76(16), 6894–6900. doi:10.1021/jo201096e
    Sponsors
    Financial support from the National Natural Science Foundation of China (21072044 to Z.J.), Excellent Youth Foundation of Henan Scientific Committee (114100510003 to Z.J.), International Cooperation Foundation of Henan Province (104300510062 to Z.J. and C.-H.T.), and ARE Grants (R-143-000-337-112 and R-143-000-342-112 to C.H.T.) is greatly appreciated.
    Publisher
    American Chemical Society (ACS)
    Journal
    The Journal of Organic Chemistry
    DOI
    10.1021/jo201096e
    PubMed ID
    21751799
    ae974a485f413a2113503eed53cd6c53
    10.1021/jo201096e
    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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