Organocatalytic Enantioselective Stereoablative Hydroxylation of 3-Halooxindoles: An Effective Method for the Construction of Enantioenriched 3-Substituted 3-Hydroxy-2-Oxindoles

Authors

  • Yu-Hua Liao,

    1. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)
    2. Graduate School of Chinese Academy of Sciences, Beijing 100049 (P.R. China)
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  • Dr. Zhi-Jun Wu,

    1. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)
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  • Wen-Yong Han,

    1. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)
    2. Graduate School of Chinese Academy of Sciences, Beijing 100049 (P.R. China)
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  • Prof. Dr. Xiao-Mei Zhang,

    1. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)
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  • Prof. Dr. Wei-Cheng Yuan

    Corresponding author
    1. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)
    • National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (P.R. China)
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Abstract

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3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme).

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