Investigation of Epimer Formation in Amide-Coupling Reactions: An Experiment for Advanced Undergraduate Students

• Autores: M. Jonathan Fray
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 91, Nº 1, 2014, págs. 136-140
• Idioma: inglés
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• Resumen

  • An experiment is described to investigate how the choice of coupling agent and reaction conditions affects the ratio of epimers formed in the sensitive amide-coupling reaction between N-Boc- or N-benzoyl-(R)-phenylglycine and (S)-valine methyl ester. The experiment, which is suitable for third-year undergraduates, is designed to teach about important synthetic methods and reaction mechanisms and to develop skills in designing experiments, data analysis, and team work.