A synthesis of 6-azabicyclo[3.2.1]octanes. The role of N-substitution.
The intramolecular cyclization reactions of aziridines with pi-nucleophiles can be a useful route to a number of heterocyclic and carbocyclic ring systems. We were particularly interested in the use of this cyclization reaction for the synthesis of 6-azabicyclo[3.2.1]octanes. We report here the development of a new synthesis of the aziridine necessary for the aziridine--pi-nucleophile cyclization. We also report on the cyclization of aziridines with three different substitutions on the aziridine nitrogen. We have found that N-diphenylphospinyl and N-H aziridines, while participating in the initial ring-opening reaction, do not lead to the desired bicyclic ring systems. In contrast, a nosyl group on the aziridine nitrogen leads efficiently to the bicyclic ring system and can be readily deprotected.
Pulipaka
Aravinda B
AB
Department of Chemistry and Biochemistry, Clippinger Laboratories, Ohio University, Athens, Ohio 45701, USA.
Bergmeier
Stephen C
SC
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009795:Octanes / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D001643:Bridged Bicyclo Compounds; D009795:Octanes