Spirocyclic Amide Acetal Synthesis by [CpRu]‐Catalyzed Condensations of α‐Diazo‐β‐Ketoesters with γ‐Lactams

Spirocyclic Amide Acetal Synthesis by [CpRu]‐Catalyzed Condensations of α‐Diazo‐β‐Ketoesters with γ‐Lactams

The synthesis of spirocyclic amide acetals (33–93 %) has been achieved through Ru(II)‐catalyzed condensations of N‐carbamate protected pyrrolidinones with metal carbenes derived from α‐diazo‐β‐ketoesters. Thanks to the mildness of the diazo decomposition conditions induced by a 1 : 1 combination of...

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Veröffentlicht in:Helvetica chimica acta 2021-10, Vol.104 (10), p.n/a
Hauptverfasser: Pertschi, Romain, Brun, Elodie, Aguirre, Adiran, Guénée, Laure, Poblador‐Bahamonde, Amalia I., Lacour, Jérôme
Format: Artikel
Sprache:eng
Schlagworte:
[CpRu] catalysis
Acetals
amide acetals
Carbenes
Carbonyl compounds
carbonyl ylides
Carbonyls
Chemical synthesis
diazo decomposition
Ketoesters
spiro compounds
ylides
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Beschreibung
Zusammenfassung:The synthesis of spirocyclic amide acetals (33–93 %) has been achieved through Ru(II)‐catalyzed condensations of N‐carbamate protected pyrrolidinones with metal carbenes derived from α‐diazo‐β‐ketoesters. Thanks to the mildness of the diazo decomposition conditions induced by a 1 : 1 combination of [CpRu(MeCN)3][BArF] and 1,10‐phenanthroline, the formation of the sensitive products is possible. Full characterization of this carbonyl‐ylide mediated process is provided by DFT calculations.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.202100122