Synthesis of 5- and 6- chloropyridyl-substituted 2- azabicyclo[2.2.1]heptanes; novel epibatidine isomers

Article abstract of DOI:10.1016/S0040-4039(98)02624-0

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.