Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students

Fray, Michael J.

Abstract

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.

Citation

Fray, M. J. (2014). Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students. Journal of Chemical Education, 91(1), https://doi.org/10.1021/ed400255q

• Journal Article Type: Article
• Publication Date: Jan 14, 2014
• Deposit Date: Aug 12, 2015
• Journal: Journal of Chemical Education
• Print ISSN: 0021-9584
• Electronic ISSN: 0021-9584
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 91
• Issue: 1
• DOI: https://doi.org/10.1021/ed400255q
• Keywords: Upper-Division Undergraduate, Laboratory Instruction, Organic Chemistry, Collaborative/Cooperative Learning,; Hands-On Learning/Manipulatives, Inquiry-Based/Discovery Learning, Amides, Amino Acids, Diastereomers, NMR Spectroscopy
• Public URL: https://nottingham-repository.worktribe.com/output/721801
• Publisher URL: http://pubs.acs.org/doi/abs/10.1021/ed400255q
• Additional Information: Full text available on publisher's website.