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.

Original languageEnglish
Pages (from-to)12101-12110
JournalJournal of Organic Chemistry
Issue number18
Early online date21 Aug 2019
Publication statusPublished - 20 Sep 2019

Scopus subject areas

  • Organic Chemistry

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