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

original image

Eine neue Fusion: Die Titelreaktion wurde mithilfe eines neuartigen BOX/CuII-Katalysators realisiert. Die Reaktion gelingt mit cyclischen Enolsilylethern unterschiedlicher Größe und lässt sich auf Dienole und benzanellierte Substrate ausdehnen. Sie bietet effektiven Zugang zu 3a-Hydroxy[n.3.0]carbobicyclen, häufigen Strukturmotiven in Naturstoffen. TBDPS=tert-Butyldiphenylsilyl.

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