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Cascade Oxidative Dearomatization/Semipinacol Rearrangement: An Approach to 2-Spirocyclo-3-oxindole Derivatives

Authors

  • Jin-Bao Peng,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582
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  • Yue Qi,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582
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  • Ai-Jun Ma,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582
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  • Prof. Dr. Yong-Qiang Tu,

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582
    • State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582

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  • Fu-Min Zhang,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582
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  • Shao-Hua Wang,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582
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  • Shu-Yu Zhang

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582
    • State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China), Fax: (+86) 931-8912582

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Abstract

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A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate.

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