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Highly Enantioselective Construction of 3-Hydroxy Oxindoles through a Decarboxylative Aldol Addition of Trifluoromethyl α-Fluorinated gem-Diols to N-Benzyl Isatins

Authors

  • Dr. Ibrayim Saidalimu,

    1. Key Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai (P.R. China)
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  • Dr. Xiang Fang,

    Corresponding author
    1. Key Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai (P.R. China)
    • Xiang Fang, Key Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai (P.R. China)

      Fanhong Wu, School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai (P.R. China)

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  • Dr. Xiao-Peng He,

    1. Key Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai (P.R. China)
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  • Jing Liang,

    1. Key Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai (P.R. China)
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  • Dr. Xueyan Yang,

    1. Key Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai (P.R. China)
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  • Prof. Fanhong Wu

    Corresponding author
    1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai (P.R. China)
    • Xiang Fang, Key Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai (P.R. China)

      Fanhong Wu, School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai (P.R. China)

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  • This work is generously supported by the National Natural Science Foundation of China (Nos. 21172148, 21202044, 21202045) and Science and Technology Commission of Shanghai Municipality (No. 10540501300).

Abstract

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An organocatalytic asymmetric direct aldol addition reaction that involves cleavage of a carbon–carbon bond through the release of trifluoroacetate was developed. The protocol is wide in scope, generating the desired oxindoles of biological interest in nearly quantitative yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee) and diastereoselectivities (up to 99:1 d.r.).

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