Stereoselective syntheses of novel 4-exo-8-anti-difunctionalized-6-azabicyclo[3.2.1]octanes containing anti-iodo in the methanobridge and exofluoro, chloro, hydroxy substituents in the other larger bridge have been carried out by reaction of Selectfluor and mercuric fluoride with the appropriate halide. Retention of configuration was observed in all displacement reactions. Precursor halides were synthesized by addition/rearrangement of dihalides or halohydrins to N-alkoxycarbonyl-6-azabicyclo[2.2.2]oct-5-enes.
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