Weck, Christian, Obst, Franziska, Nauha, Elisa , Schofield, Christopher and Gruber, Tobias (2017) Synthesis of a bicyclic oxo-gamma-lactam from a simple caprolactam derivative. New Journal of Chemistry, 41 . pp. 9984-9989. ISSN 1144-0546
Full content URL: https://doi.org/10.1039/c7nj02348k
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| Item Type: | Article |
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| Item Status: | Live Archive |
Abstract
The synthesis of the 6-azabicyclo[3.2.1]octane ring system, via Dieckmann cyclization, is described. Ring closure involves reaction of a caprolactam enolate with a C-6 ester, the reactive axial conformation of which is promoted by the presence of an N-tert-butyloxycarbonyl group on the lactam nitrogen. The results will enable the synthesis of new bridged caprolactams for testing as antibacterials and nucleophilic enzyme inhibitors.
| Keywords: | caprolactam, X-ray diffraction, NMR Spectroscopy, Molecular Conformation, drug synthesis |
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| Subjects: | F Physical Sciences > F160 Organic Chemistry F Physical Sciences > F150 Medicinal Chemistry F Physical Sciences > F151 Pharmaceutical Chemistry |
| Divisions: | College of Science > School of Pharmacy |
| ID Code: | 28082 |
| Deposited On: | 02 Aug 2017 14:24 |
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