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Rhodium-Catalyzed Asymmetric Arylative Cyclization of meso-1,6-Dienynes Leading to Enantioenriched cis-Hydrobenzofurans

Authors

  • Zhi-Tao He,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Bing Tian,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    2. Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Yuki Fukui,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Prof. Dr. Xiaofeng Tong,

    1. Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China)
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  • Prof. Dr. Ping Tian,

    Corresponding author
    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    • Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Prof. Guo-Qiang Lin

    Corresponding author
    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
    • Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Financial support for this work was generously provided by the 973 Program (2010CB833302), NSFC (21232009, 21102161), and the Chinese Academy of Sciences (CAS). We thank Dr. Hanqing Dong for helpful discussions.

Abstract

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In tandem: The title reaction of cyclohexadienone-containing meso-1,6-dienynes with arylboronic acids through a tandem arylrhodation/conjugate addition sequence has been realized, and provides a novel approach to the enantioenriched cis-hydrobenzofurans with both excellent yields and enantioselectivities. binap=2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl, Boc=tert-butoxycarbonyl.

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