
New Journal of Chemistry p. 9984 - 9989 (2017)
Update date:2022-08-16
Topics:
Weck, Christian
Obst, Franziska
Nauha, Elisa
Schofield, Christopher J.
Gruber, Tobias
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.
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