Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks

Nicola Piens, Kristof Van Hecke, Dieter Vogt, Matthias D'hooghe

Research output: Contribution to journalArticlepeer-review

Abstract

The Co2(CO)8-catalyzed carbonylation of different classes of non-activated aziridines with diverse substitution patterns was investigated. Special attention was devoted to selectivity issues and reaction optimization. This study resulted in the regio- and stereospecific synthesis of 24 novel β-lactam target structures in high yields on a multigram scale. The synthetic potential of the newly obtained azetidin-2-ones was illustrated via ring-expansion, ring-closure, and/or side chain-functionalization protocols to provide a straightforward entry to novel pyrrolidines, C-fused bi- and tricyclic β-lactams and monocyclic carbapenem analogs.

Original languageEnglish
Pages (from-to)4816-4821
Number of pages6
JournalOrganic & Biomolecular chemistry
Volume15
Issue number22
DOIs
Publication statusPublished - 22 May 2017

Keywords

  • Journal Article

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