Aza-annulation of enaminones with itaconic anhydride: kinetic preference for exocyclic enamide products

M Hadden, M Nieuwenhuyzen, D Potts, PJ Stevenson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Enaminones react with itaconic anhydride in methylene chloride at room temperature to give exocyclic enamides sis the major products. These can be readily equilibrated to the thermodynamically more stable endocyclic enamides. In substrates where the exocyclic isomer could not be formed only intractable materials were produced from this reaction. An intermediate in this two step process was detected and identified by proton and C-13 NMR spectroscopy. In two cases chiral enaminones were employed and the relative stereochemistry at the new chiral centre in the product was established by a crystal structure of compound 27.

Original languageEnglish
Pages (from-to)3437-3441
Number of pages5
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number20
Publication statusPublished - 21 Oct 1998

Keywords

  • QUATERNARY CARBON CENTERS
  • CHIRAL BETA-ENAMINOESTERS
  • MICHAEL-TYPE ALKYLATION
  • ACRYLATE DERIVATIVES
  • STEREOCONTROLLED ELABORATION
  • ENANTIOSELECTIVE SYNTHESIS
  • SECONDARY ENAMINES
  • TRANSITION-STATE
  • IMINES
  • (+)-VINCAMINE

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