A process for cleaving cinchona alkaloids to a quinoline derivative and an enantiomerically pure, functionalized 1-azabicyclo(2.2.2)octane, includes treating a cinchona alkaloid with a complex metal hydride while simultaneously oxidizing by exposure to air in an ether or tetrahydrofuran. Enantiomerically pure 1-azabicyclo(2.2.2)octanes of the formula ##STR1## in which R is hydrogen, a straight-chain or branched alkoxycarbonyl group with 1 to 12 carbon atoms, a straight-chain or branched alkyl group with 1 to 12 carbon atoms, alkylated silyl groups, or a substituted phenyl or benzyl substituent, are also provided.

Amino secondary alcohols, e.g. cinchona alkaloid such as quinine, epiquinine, quinidine, epiquinidine and mixtures thereof, are oxidized to quininone, i.e., a mixture of quininone and quinidinone, by reaction of the alcohols with a metal ketyl, in an inert hydrocarbon solvent. The ketyl is formed through the reaction of an alkali metal or amalgam with a diphenyl ketone, such as benzophenone or fluorenone.

Quinidinone is reduced to quinidine through reaction with a reducing agent, selected from aklyl-substituted aluminum hydrides or alkali metal alkyl-substituted aluminum hydrides, in the presence of a stereospecific orienting agent, such as pyridine.