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

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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.

Item Type: Article
RIS ID: https://nottingham-repository.worktribe.com/output/721801
Additional Information: Full text available on publisher's website.
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
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1021/ed400255q
Depositing User: Fray, Dr M. Jonathan
Date Deposited: 12 Aug 2015 09:41
Last Modified: 04 May 2020 16:41
URI: http://eprints.nottingham.ac.uk/id/eprint/2283

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