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    Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

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    Type
    Article
    Authors
    Yang, Wenguo
    Tan, Davin
    Lee, Richmond
    Li, Lixin
    Pan, Yuanhang
    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
    2012-02-08
    Online Publication Date
    2012-02-08
    Print Publication Date
    2012-04
    Permanent link to this record
    http://hdl.handle.net/10754/562090
    
    Metadata
    Show full item record
    Abstract
    Through the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
    Sponsors
    Financial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) to Z.J., International Cooperation Foundation of Henan Province (104300510062) to Z.J. and C. H. T. and KAUST (4000000076) to K.-W. H. are greatly appreciated.
    Publisher
    Wiley
    Journal
    Chemistry - An Asian Journal
    DOI
    10.1002/asia.201100863
    PubMed ID
    22318922
    ae974a485f413a2113503eed53cd6c53
    10.1002/asia.201100863
    Scopus Count
    Collections
    Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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