One-step Preparation of N-Unprotected Aziridines from 2<i>H</i>-Azirines by Addition of Ketene Silyl Acetals Catalyzed by Lewis Acids

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  • Itaru Suzuki
    Research Center for Environmental Preservation, Osaka University, 2-4 Yamada-oka, Suita, Osaka 565-0871 , Japan
  • Yuya Takenaka
    Research Center for Environmental Preservation, Osaka University, 2-4 Yamada-oka, Suita, Osaka 565-0871 , Japan
  • Yoshitaka Morishita
    Research Center for Environmental Preservation, Osaka University, 2-4 Yamada-oka, Suita, Osaka 565-0871 , Japan
  • Ikuya Shibata
    Research Center for Environmental Preservation, Osaka University, 2-4 Yamada-oka, Suita, Osaka 565-0871 , Japan

Abstract

<jats:title>Abstract</jats:title> <jats:p>The nucleophilic addition of ketene silyl acetals 2 into 2H-azirines 1 proceeded in the presence of Lewis acids such as InX3 or Sc(OTf)3 to give N-unprotected aziridines 3. The mild Lewis acidity of the catalyst is important for the achievement of this coupling. The generated aziridine 3 could then be transformed into either oxazolines or γ–amino carbonyls.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 51 (1), 9-12, 2021-10-14

    Oxford University Press (OUP)

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