Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students
Fray, Michael J. (2014) Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students. Journal of Chemical Education, 91 (1). pp. 136-140. ISSN 0021-9584
Official URL: http://pubs.acs.org/doi/abs/10.1021/ed400255q
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.
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