Catalytic and Enantioselective α-Functionalization of Oxindoles Through Oxidative Reactions with Naphthoquinones

Authors

  • Woon-Yew Siau,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691
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  • Wenjun Li,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691
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  • Fei Xue,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691
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  • Qiao Ren,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691
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  • Prof. Minghu Wu,

    1. College of Chemistry and Biology Sciences, Xianning University, Hubei Province, 437100 (P.R. China)
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  • Prof. Shaofa Sun,

    1. College of Chemistry and Biology Sciences, Xianning University, Hubei Province, 437100 (P.R. China)
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  • Prof. Haibing Guo,

    Corresponding author
    1. College of Chemistry and Biology Sciences, Xianning University, Hubei Province, 437100 (P.R. China)
    • College of Chemistry and Biology Sciences, Xianning University, Hubei Province, 437100 (P.R. China)
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  • Prof. Xuefeng Jiang,

    Corresponding author
    1. Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, 3663N Zhongshan Road, Shanghai, 200062 (P.R. China), Fax: (+86) 21-52133654
    • Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, 3663N Zhongshan Road, Shanghai, 200062 (P.R. China), Fax: (+86) 21-52133654
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  • Prof. Dr. Jian Wang

    Corresponding author
    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691
    • Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691
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Abstract

original image

Strong as an oxindole: The enantioselective assembly of 3,3-disubstituted oxindoles is an attractive and valuable target because of the unique properties of the oxindole core. A new organocatalyzed and enantioselective aerobic oxidative strategy for the assembly of this core structure from oxindoles and simple naphthoquinones is reported (see scheme).

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