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Highly Enantioselective [3+2] Annulation of Cyclic Enol Silyl Ethers with Donor–Acceptor Cyclopropanes: Accessing 3a-Hydroxy [n.3.0]Carbobicycles

Authors

  • Hao Xu,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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    • These authors contributed equally to this work.

  • Jian-Ping Qu,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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    • These authors contributed equally to this work.

  • Dr. Saihu Liao,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Hu Xiong,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Prof. Dr. Yong Tang

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • We are grateful for the financial support from the National Natural Sciences Foundation of China (20932008 and 21121062), the Major State Basic Research Development Program (Grant No. 2009CB825300), and the Chinese Academy of Sciences.

Abstract

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A new fuse: The title reaction was realized using a new bisoxazoline (BOX)/CuII catalyst. This reaction works well with cyclic enol silyl ethers of different sizes, and can be extended to dienol and benzene-fused substrates, thus providing an effective and general access to a range of 3a-hydroxy [n.3.0]carbobicycles which are found as a core structure in many natural products. TBDPS=tert-butyldiphenylsilyl.

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