Abstract: | Quaternary 1-2-(adamantan-1-yl)ethyl]pyridinium bromides were reduced with sodium tetrahydridoborate in ethanol, and hydroarylation of the resulting 1-2-(adamantan-1-yl)ethyl]-1,2,3,6-tetrahydropyridines with benzene in trifluoromethanesulfonic acid afforded phenylpiperidines with preferentially equatorial orientation of the phenyl substituent. |