Synthesis of a bicyclic oxo-γ-lactam from a simple caprolactam derivative

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 nitro...

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Bibliographic Details
Published in:New journal of chemistry 2017, Vol.41 (18), p.9984-9989
Main Authors: Weck, Christian, Obst, Franziska, Nauha, Elisa, Schofield, Christopher J., Gruber, Tobias
Format: Article
Language:English
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Summary: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.
ISSN:1144-0546
1369-9261
DOI:10.1039/C7NJ02348K