Synthesis of a bicyclic oxo-γ-lactam from a simple caprolactam derivativeElectronic supplementary information (ESI) available. CCDC 1528320 (1b) and 1522636 (3). For synthetic procedures, crystallographic and spectroscopic data. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7nj02348k

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
Main Authors: Weck, Christian, Obst, Franziska, Nauha, Elisa, Schofield, Christopher J, Gruber, Tobias
Format: Article
Language:English
Online Access:Get full text
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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. Reaction of caprolactams with an axial ester substituent with base gives the 6-azabicyclo-[3.2.1]octane ring system via Dieckmann cyclization.
ISSN:1144-0546
1369-9261
DOI:10.1039/c7nj02348k