Highly Efficient Enantioselective Construction of Bispirooxindoles Containing Three Stereocenters through an Organocatalytic Cascade Michael–Cyclization Reaction

Authors

  • Hao Wu,

    1. State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23504439
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  • Li-Li Zhang,

    1. Key Laboratory of Systems Bioengineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072 (P.R. China)
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  • Zhi-Qing Tian,

    1. State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23504439
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  • Dr. Yao-Dong Huang,

    Corresponding author
    1. Key Laboratory of Systems Bioengineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072 (P.R. China)
    • Key Laboratory of Systems Bioengineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072 (P.R. China)
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  • Prof. Yong-Mei Wang

    Corresponding author
    1. State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23504439
    • State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23504439
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Abstract

Bispirooxindole derivatives containing three stereocenters, including two spiro quaternary centers, were synthesized in a high-yielding, atypically rapid, and stereocontrolled cascade Michael–cyclization reaction between methyleneindolinones and isothiocyanato oxindoles catalyzed by a bi- or multifunctional organocatalyst. Mild conditions were used to construct bispirooxindoles with excellent enantio- and diastereomeric purities within less than 1 min. Catalyst reconfiguration offered access to the opposite enantiomer. This exceptionally highly efficient procedure will allow diversity-oriented syntheses of this intriguing class of compounds with potential biological activities.

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