Synthesis of Enantioenriched β-Hydroxy-γ-Acetal Enamides by Rhodium-Catalyzed Asymmetric Transfer Hydrogenation
Anne Westermeyer, Gérard Guillamot, Phannarath Phansavath, Virginie Ratovelomanana‐Vidal
Abstract
The asymmetric reduction of β-keto-γ-acetal enamides has been investigated. A wide range of enantioenriched β-hydroxy-γ-acetal enamides were obtained through asymmetric transfer hydrogenation catalyzed by a tethered Rh(III)-DPEN complex with yields up to quantitative and enantioselectivities up to 99%. The reaction proved to be highly chemoselective toward the reduction of the carbonyl group over the C═C bond.
Topics & Concepts
AcetalChemistryTransfer hydrogenationRhodiumCatalysisEnantioselective synthesisCombinatorial chemistryOrganic chemistryRutheniumAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisCatalytic C–H Functionalization Methods