One-Pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro-Stereocenters

Authors

  • Yun-Lin Liu,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
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  • Prof. Dr. Xin Wang,

    1. College of Chemistry, Sichuan University, Chengdu, 610064 (China)
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  • Yu-Lei Zhao,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
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  • Feng Zhu,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
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  • Xing-Ping Zeng,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
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  • Long Chen,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
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  • Prof. Dr. Cui-Hong Wang,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
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  • Prof. Dr. Xiao-Li Zhao,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
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  • Prof. Dr. Jian Zhou

    Corresponding author
    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)
    • Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China)

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  • The financial support from the 973 program (2011CB808600), NSFC (21172075, 21222204), Ministry of Education (NCET-11-0147 and PCSIRT), and Program of SSCS (13XD1401600) is appreciated.

Abstract

original image

Immer der Reihe nach: Eine organokatalytische Sequenz aus Morita-Baylis-Hillman(MBH)-Reaktion, Bromierung und [3+2]-Ringschluss führt hoch stereoselektiv zu Bis(spirooxindolen) mit benachbarten Spiro-Stereozentren. Der Schlüsselschritt dabei ist der katalytische asymmetrische [3+2]-Ringschluss zwischen von Isatinen abgeleiteten MBH-Addukten, die eine vierfach substituierte Doppelbindung tragen, und weiteren Isatinderivaten.

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