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

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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.

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

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Publication details

The article was received on 30 Jun 2017, accepted on 27 Jul 2017 and first published on 04 Aug 2017


Article type: Paper
DOI: 10.1039/C7NJ02348K
Citation: New J. Chem., 2017, Advance Article
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    Synthesis of a bicyclic oxo-γ-lactam from a simple caprolactam derivative

    C. Weck, F. Obst, E. Nauha, C. J. Schofield and T. Gruber, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ02348K

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