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

[img] PDF - Repository staff only - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader
Download (1MB)

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
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 Campus > Faculty of Science > School of Chemistry
Depositing User: Fray, Dr M. Jonathan
Date Deposited: 12 Aug 2015 09:41
Last Modified: 15 May 2016 19:01
URI: http://eprints.nottingham.ac.uk/id/eprint/2283

Actions (Archive Staff Only)

Edit View Edit View