In the asymmetric synthesis of chiral compounds, the reduction of prochiral unsaturated reactants has a great importance. (S)-proline as a chiral auxiliary is used in the hydrogenations of exocyclic α,β-unsaturated ketones with palladium on carbon catalysts, producing the corresponding saturated ketones with an optical purity up to 20%. The influence of the parameters (solvents, additives) on the optical yield is also investigated. The highest enantioselectivity was obtained in ethyl acetate and acetonitrile (ee 20%), at atmospheric pressure and room temperature.
- Enantiomeric excess
- Enantioselective hydrogenation
- Exocyclic α,β-unsaturated
- Palladium catalyst
ASJC Scopus subject areas
- Process Chemistry and Technology
- Physical and Theoretical Chemistry