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The coupling of N-protected 2-azabicyclo[2.2.1]hept-5-enes and 2-chloro-5-iodopyridine under reductive Heck conditions gives approximately equal amounts of exo-5- and exo-6- (6'-chloro-3'-pyridyl)-2-azabicyclo-[2.2.1]heptanes. The ratio varies slightly under a range of conditions but both products are isolated in every case (and in the corresponding reaction with 3-iodopyridine) contrary to a recent...
A synthetic route to the epibatidine analogue endo-5-(6-chloro-3-pyridyl)-2-azabicyclo[2.2.1]heptane and the corresponding endo-6- isomer is described, starting from a readily-available 2-azabicyclo[2.2.1]hept-5-ene derivative. Both the exo-5- and exo-6- compounds are also shown to be accessible from the same substrate using reductive Heck chemistry.
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