T. Heugebaert, Joke Van Hevele, Wouter Couck
Feb 1, 2010
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Influential Citations
10
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Journal
European Journal of Organic Chemistry
Abstract
This paper presents the synthesis of epibatidine analogues by a straightforward one-pot method for the synthesis of 7-azabicyclo[2.2.1]heptane-1-carbonitriles, starting from cyclohexanones bearing a leaving group at the 4-position. In situ imine formation, followed by reversible cyanide addition, allows complete conversion of 4-(mesyloxy)cyclohexanone to the bicyclic core. Elaboration of the introduced nitrile functionality and deprotection of the tertiary amine leads to five new epibatidine analogues.