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

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...

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Veröffentlicht in:Chemistry letters 2022-01, Vol.51 (1), p.9-12
Hauptverfasser: Suzuki, Itaru, Takenaka, Yuya, Morishita, Yoshitaka, Shibata, Ikuya
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.210589