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Gold-Catalyzed Rearrangement of Allylic Oxonium Ylides: Efficient Synthesis of Highly Functionalized Dihydrofuran-3-ones

Authors

  • Junkai Fu,

    1. Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055 (China)
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  • Dr. Hai Shang,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Zhaofeng Wang,

    1. Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055 (China)
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  • Dr. Le Chang,

    1. Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055 (China)
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  • Wenbing Shao,

    1. Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055 (China)
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  • Prof. Dr. Zhen Yang,

    Corresponding author
    1. Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055 (China)
    • Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055 (China)
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  • Prof. Dr. Yefeng Tang

    Corresponding author
    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
    • The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • We acknowledge financial support from the National Science Foundation of China (21102081, 21272133), New Teachers’ Fund for Doctor Stations, Ministry of Education (20110002120011), and opening foundation of Laboratory of Chemical Genomics, Peking University of Shenzhen Graduate School. We thank Dr. Tuoping Luo (H3 Biomedicine Inc., MA (USA)) and Prof. Zhigang Wang (Peking University) for the helpful discussions.

Abstract

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“Diazo” not needed: The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3-sigmatropic rearrangement, or a stepwise 1,4-allyl migration followed by a Claisen rearrangement (see scheme).

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