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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.

Original publication

DOI

10.1039/b814450h

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/02/2009

Volume

7

Pages

518 - 526

Keywords

Alanine, Kinetics, Models, Molecular, Molecular Conformation, Oxazolidinones, Stereoisomerism, Substrate Specificity, Temperature, Thermodynamics