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Diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles using both aldonitrones and ketonitrones

Author

Listed:
  • Peng-Wei Xu

    (East China Normal University)

  • Jia-Kuan Liu

    (Nanjing University)

  • Lan Shen

    (Nanjing University)

  • Zhong-Yan Cao

    (East China Normal University)

  • Xiao-Li Zhao

    (East China Normal University)

  • Jun Yan

    (Nanjing University)

  • Jian Zhou

    (East China Normal University
    East China Normal University
    Nankai University)

Abstract

Optically active spirocyclic compounds play an important role in drug discovery, and new synthetic strategies for the efficient generation of spiro stereocenters are in much demand. Here we report a catalytic enantioselective cycloaddition using spirocyclic donor–acceptor cyclopropanes as a promising approach for the generation of spiro stereocenters. A diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles with both aldonitrones and ketonitrones is developed. The key to reaction development is the activation of spirocyclopropyl oxindoles by a suitable electron-withdrawing N-protecting group. This activation approach offers the promise of a general solution to enable spirocyclopropyl oxindoles as synthons for catalytic enantioselective synthesis of spirocyclic oxindoles featuring a C3 spiro stereocenter, a prominent structural motif in drugs and pharmaceutically active compounds. This protocol also constitutes the catalytic enantioselective reaction using unactivated achiral ketonitrones to construct tetrasubstituted carbon stereocenters.

Suggested Citation

  • Peng-Wei Xu & Jia-Kuan Liu & Lan Shen & Zhong-Yan Cao & Xiao-Li Zhao & Jun Yan & Jian Zhou, 2017. "Diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles using both aldonitrones and ketonitrones," Nature Communications, Nature, vol. 8(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_s41467-017-01451-1
    DOI: 10.1038/s41467-017-01451-1
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