Formation of 3-azabicyclo[3.3.1]non-3-enes: Imino amides vs. imino alkenes

Publication Type:
Journal Article
Citation:
Monatshefte fur Chemie, 2014, 145 (6), pp. 983 - 992
Issue Date:
2014-01-01
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Formation of 3-azabicyclo[3.3.1]non-3-enes imino amides vs. imino alkenes.pdfPublished Version963.68 kB
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An effective method for synthesising alkaloid-like compounds containing the 3-azabicyclo[3.3.1]non-3-ene core structure was successfully carried out in a stereoselective manner via the bridged-Ritter reactions. Important optically active 6-alkyl(aryl)amido-4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]non- 3-enes (imino amides) and 4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]nona- 3,6-dienes (imino alkenes) were obtained in one step from (-)-β-pinene and the respective nitriles in the presence of concentrated H2SO 4. The relative compositions of these products were controlled by varying the reaction conditions. Kinetic studies were conducted to enable a mechanistic understanding of the reaction pathways. Graphical Abstract: [Figure not available: see fulltext.] © 2014 Springer-Verlag Wien.
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