Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students
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...
| Main Author: | |
|---|---|
| Format: | Article |
| Published: |
American Chemical Society, Division of Chemical Education
2014
|
| Subjects: | |
| Online Access: | https://eprints.nottingham.ac.uk/2283/ |
| _version_ | 1848790745952026624 |
|---|---|
| author | Fray, Michael J. |
| author_facet | Fray, Michael J. |
| author_sort | Fray, Michael J. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T18:17:30Z |
| format | Article |
| id | nottingham-2283 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T18:17:30Z |
| publishDate | 2014 |
| publisher | American Chemical Society, Division of Chemical Education |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-22832020-05-04T16:41:50Z https://eprints.nottingham.ac.uk/2283/ Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students Fray, Michael J. 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. American Chemical Society, Division of Chemical Education 2014-01-14 Article PeerReviewed 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 Upper-Division Undergraduate Laboratory Instruction Organic Chemistry Collaborative/Cooperative Learning Hands-On Learning/Manipulatives Inquiry-Based/Discovery Learning Amides Amino Acids Diastereomers NMR Spectroscopy http://pubs.acs.org/doi/abs/10.1021/ed400255q doi:10.1021/ed400255q doi:10.1021/ed400255q |
| spellingShingle | Upper-Division Undergraduate Laboratory Instruction Organic Chemistry Collaborative/Cooperative Learning Hands-On Learning/Manipulatives Inquiry-Based/Discovery Learning Amides Amino Acids Diastereomers NMR Spectroscopy Fray, Michael J. Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students |
| title | Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students |
| title_full | Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students |
| title_fullStr | Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students |
| title_full_unstemmed | Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students |
| title_short | Investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students |
| title_sort | investigation of epimer formation in amide coupling reactions: an experiment for advanced undergraduate students |
| topic | Upper-Division Undergraduate Laboratory Instruction Organic Chemistry Collaborative/Cooperative Learning Hands-On Learning/Manipulatives Inquiry-Based/Discovery Learning Amides Amino Acids Diastereomers NMR Spectroscopy |
| url | https://eprints.nottingham.ac.uk/2283/ https://eprints.nottingham.ac.uk/2283/ https://eprints.nottingham.ac.uk/2283/ |