CATALYTIC ASYMMETRIC SYNTHESES. Part III. Asymmetric Hydrogenation of Piperitenone Catalysed by Chiral Ruthenium Hydrides: An Example of a Catalytic Kinetic Resolution.

Article abstract of DOI:10.1016/S0040-4020(01)85919-6

Piperitenone has been hydrogenated in the presence of chiral ruthenium catalysts to give piperitone, menthone and isomenthone.Starting from piperitone (42 percent e.e.) excellent selectivity (80 percent e.e.) was obtained with menthone.The mechanism of the reaction, a double asymmetric synthesis, is discussed with respect to kinetic resolution of piperitone as well as the effect of the chiral center in the substrate on the catalytic asymmetric induction.