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Synthesis 2018; 50(09): 1820-1826
DOI: 10.1055/s-0036-1591920
DOI: 10.1055/s-0036-1591920
paper
Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one Oximes
This work was partly supported by a Grant-in-Aid for Scientific Research on Innovative Areas ‘Advanced Molecular Transformations by Organocatalysis’ (No. 23105011) from MEXT, ‘Precisely Designed Catalysts with Customized Scaffolding’ (No. JP16H00998) from JSPS, and Life Science Research (Platform for Drug Discovery, Informatics, and Structural Life Science) from the Japan Agency for Medical Research and Development (AMED), Japan.Further Information
Publication History
Received: 05 December 2017
Accepted after revision: 05 January 2018
Publication Date:
05 February 2018 (online)
![](https://www.thieme-connect.de/media/synthesis/201809/lookinside/thumbnails/ss-2017-f0782-op_10-1055_s-0036-1591920-1.jpg)
Abstract
An efficient synthesis of 1-aminoadamantane (amantadine) derivatives is described. This synthesis features acid-promoted aza-Prins cyclization of 7-methylenebicyclo[3.3.1]nonan-3-one oximes, which are readily prepared from 1,3-adamantanediol via a Grob fragmentation and the subsequent oximation, to give various 3-substituted 1-(alkoxyamino)adamantanes. After the reduction of alkoxyamines, not only 3-substituted 1-aminoadamantanes, but also chiral 2,5-disubstituted derivatives were obtained in good yields.
Key words
1-aminoadamantanes - amantadine - 1-(alkoxyamino)-adamantanes - aza-Prins reaction - oximeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591920.
- Supporting Information
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For selected examples, see:
Recently, few examples of palladium-catalyzed adamantane methylene C–H functionalization have been reported, see: