A synthesis of 6-azabicyclo[3.2.1]octanes. The role of N-substitution
| Autor: | Stephen C. Bergmeier, Aravinda B. Pulipaka |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
Magnetic Resonance Spectroscopy
Intramolecular reaction Bicyclic molecule Spectrophotometry Infrared Stereochemistry Organic Chemistry Substitution (logic) Intramolecular cyclization Aziridine Ring (chemistry) Octanes Chemical synthesis Mass Spectrometry chemistry.chemical_compound Bridged Bicyclo Compounds chemistry Nucleophile |
| Zdroj: | The Journal of organic chemistry. 73(4) |
| ISSN: | 0022-3263 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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