Synthesis of Isomeric Hexahydro- and Perhydroisoindol-1-ones

Sa？etak Catalytic hydrogenation of triethyl 2-cyanocyclohex-1-(XIV) and -2(XV)-ene-1,5,5-tricarboxylates yielded the corresponding 2- -cyanocyclohexane (XVII) and diethyl perhydroisoindol-1-one-6,6- -dicarboxylate (V), the latter being formed through spontaneous intramolecular cyclisation of triethyl 2-aminomethylcyclohexane- 1,5,5-tricarboxylate (XXI). Regiospecific reductions and isomerisations of cyanocyclohexenes (XIV) and (XV), and their conversion into corresponding hexahydroisoindol-1-ones (IV) and (III) were shown to depend on the hydrogenating conditions and catalysts