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

Fray, Michael J.

Authors

Michael J. Fray jonathan.fray@nottingham.ac.uk

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.

Journal Article Type Article
Publication Date Jan 14, 2014
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
Institution 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), doi:10.1021/ed400255q
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
Publisher URL http://pubs.acs.org/doi/abs/10.1021/ed400255q
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information Full text available on publisher's website.

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