Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

Francisco Alonso, Stephen G. Davies, Almut S. Elend, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A range of ferrocenylimines derived from ferrocenecarboxaldehyde and the a-amino acids (S)-alanine, (S)-2-aminobutyric acid, (S)-norvaline, (R)-2-phenylglycine, (S)-phenylalanine, O-benzyl (S)-serine, and (S)-tryptophan can be cyclised stereoselectively to afford either the corresponding cis- or trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones. The cyclisation reaction shows marked temperature dependence, giving rise preferentially to the trans-oxazolidinone under kinetic control (-78 degrees C) and the thermodynamic cis-oxazolidinone at -15 degrees C to rt.

Original languageEnglish
Pages (from-to)518-526
Number of pages9
JournalOrganic & Biomolecular Chemistry
Volume7
Issue number3
DOIs
Publication statusPublished - 2009

Keywords

  • ALPHA-AMINO-ACIDS
  • SELF-REGENERATION
  • ENANTIOSPECIFIC SYNTHESIS
  • ENANTIOMERICALLY PURE
  • DERIVATIVES
  • TRYPTOPHAN
  • ALDEHYDES
  • ALANINE
  • REPRODUCTION
  • N,O-ACETALS

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