title: Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones.
abstract: A range of ferrocenylimines derived from ferrocenecarboxaldehyde and the alpha-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.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UKOX1 3TA.
authors.forename: Francisco
authors.initials: F
authors.lastname: Alonso
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: Almut S
authors.initials: AS
authors.lastname: Elend
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D000409:Alanine / Q000737:chemistry; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature; D013816:Thermodynamics
chemical_list: D023303:Oxazolidinones; D000409:Alanine