Synthesis of γ‑Lactams by Formal Cycloadditions with Ketenes

Synthesis of γ‑Lactams by Formal Cycloadditions with Ketenes

The synthesis of γ-lactams is reported by a formal (3+2) cycloaddition between readily available ketenes and aziridines or a one-pot formal (2+1+2) cycloaddition using imines as aziridine precursors. The method is practical, is scalable, and affords high yields. It also offers a high level of regio-...

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Veröffentlicht in:Organic letters 2021-04, Vol.23 (7), p.2449-2454
Hauptverfasser: Viceriat, Audrey, Marchand, Isabelle, Carret, Sébastien, Poisson, Jean-François
Format: Artikel
Sprache:eng
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Chemical Sciences
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Zusammenfassung:The synthesis of γ-lactams is reported by a formal (3+2) cycloaddition between readily available ketenes and aziridines or a one-pot formal (2+1+2) cycloaddition using imines as aziridine precursors. The method is practical, is scalable, and affords high yields. It also offers a high level of regio- and diastereoselectivity on a wide range of substrates as well as a high stereoselectivity in the case of enantiopure aziridines.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00335