N-Heterocyclic carbene catalysed β-lactam synthesis

Nicolas Fabien Denis Duguet, Craig Donald Campbell, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

223 Citations (Scopus)

Abstract

N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding beta-lactams in good to excellent isolated yields; chiral NHCs give beta-lactams in high e. e. after crystallisation.

Original languageEnglish
Pages (from-to)1108-1113
Number of pages6
JournalOrganic & Biomolecular Chemistry
Volume6
Issue number6
Early online date12 Feb 2008
DOIs
Publication statusPublished - 2008

Keywords

  • DIELS-ALDER REACTIONS
  • ASYMMETRIC-SYNTHESIS
  • STAUDINGER REACTION
  • DIRECT ANNULATIONS
  • AMINO-ACIDS
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • ENANTIOSELECTIVE SYNTHESIS
  • GAMMA-BUTYROLACTONES
  • ENALS
  • IMINES

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