Highly Diastereoselective Multicomponent Cascade Reactions: Efficient Synthesis of Functionalized 1-Indanols

Authors

  • Jun Jiang,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Xiaoyu Guan,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Shunying Liu,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Baiyan Ren,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Xiaochu Ma,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Xin Guo,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Fengping Lv,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Xiang Wu,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • Prof. Wenhao Hu

    Corresponding author
    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
    • Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 (China)
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  • We greatly thank NSFC (nos 21125209 and 20932003) and MOST (2011CB808600) for financial support.

Abstract

original image

Trapped: A Michael-aldol-type cascade reaction including the trapping of an oxonium ylide through a delayed proton shift leads to the formation of multiple stereocenters in a mild one-pot synthesis. Enantiomerically pure indanol derivatives with four stereocenters and a stereogenic quaternary carbon center were easily obtained through this method in moderate to good yields.

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