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Trifluoromethylation of Aromatic Isoxazoles: Regio- and Diastereoselective Route to 5-Trifluoromethyl-2-isoxazolines

Authors

  • Hiroyuki Kawai,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • Kentaro Tachi,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • Etsuko Tokunaga,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • Dr. Motoo Shiro,

    1. Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima, Tokyo 196-8666 (Japan)
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  • Prof. Norio Shibata

    Corresponding author
    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
    • Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan)
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  • This study was financially supported in part by Kakenhi (21390030, 22106515). We also thank TOSOH F-TECH INC. for a gift of Me3SiCF3.

Abstract

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Addieren leicht gemacht: Die Aktivierung aromatischer Isoxazole durch eine Nitrogruppe in 4-Stellung führte zur ersten regio- und diastereoselektiven Trifluormethylierung von Isoxazolen in 5-Stellung über eine nucleophile Addition mit Me3SiCF3 (siehe Schema; DMF=N,N′-Dimethylformamid). Der Prozess eignet sich für zahlreiche in 3- und 5-Stellung substituierte Substrate.

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