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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M. Jonathan Fray (2013) studied this question.
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