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Synthesis 2010(3): 493-497
DOI: 10.1055/s-0029-1217137
DOI: 10.1055/s-0029-1217137
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Approach to Azabicyclo[n.3.1]alkanes by Double Mannich Reaction
Weitere Informationen
Received
29 September 2009
Publikationsdatum:
20. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
20. November 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/201003/lookinside/thumbnails/10.1055-s-0029-1217137-1.jpg)
Abstract
Chlorotrimethylsilane-promoted double Mannich annulation of ketones using N,N-bis(methoxymethyl)benzylamine has been explored. It has been shown that the structure of the substrate drastically influenced the outcome of the reaction. The method allows azabicyclo[n.3.1]alkane derivatives (n = 2-5) to be obtained in good yields.
Key words
annulation - Mannich bases - molecular rigidity - bicyclic compounds - chlorotrimethylsilane
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