Asymmetric hydrogenation of prochiral and kinetic resolution of chiral cyclohexanone derivatives with Pd catalysts

This paper focuses on the investigation of the role of catalytic and molecular factors determining the optical yield in the enantioselective hydrogenation of C=C double bonds in prochiral unsaturated ketones and in the kinetic resolution of racemates of chiral cyclic ketones with proline mediated reductive alkylation. The hydrogenation of two unsaturated methyl cyclohexenones, and the kinetic resolution of two saturated methyl cyclohexanones with proline were studied with different Pd catalysts. The aim was to find out the effects of catalyst modifiers and chiral auxiliary, beside that of the structure and the degree of substitution of the substrates on the stereochemical outcome and yield of these reactions.