α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis.
Journal
The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R
Informations de publication
Date de publication:
20 09 2019
20 09 2019
Historique:
pubmed:
23
8
2019
medline:
23
8
2019
entrez:
22
8
2019
Statut:
ppublish
Résumé
Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.
Identifiants
pubmed: 31433643
doi: 10.1021/acs.joc.9b02030
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM