Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori–Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds
Guilherme S. Caleffi, Juliana de Oliveira Carneiro Brum, Angela T. Costa, Jorge L. O. Domingos, Paulo R. R. Costa
Abstract
3-Arylidenechroman-4-ones and 2-arylidene-1-tetralones are hydrogenated to cis-benzylic alcohols in dr’s and er’s up to 99:1 via a C═C and C═O one-pot reduction in the presence of 2–5 mol % Noyori–Ikariya-type RuII chiral complexes and HCO2Na as a hydrogen source under asymmetric transfer hydrogenation–dynamic kinetic resolution (ATH-DKR) conditions. The oxidation of theses substrates resulted in the enantioselective synthesis of the natural homoisoflavanone dihydrobonducellin and its carba-analogues.
Topics & Concepts
TetralonesEnantioselective synthesisTransfer hydrogenationChemistryNoyori asymmetric hydrogenationKinetic resolutionCatalysisMedicinal chemistryStereochemistryOrganic chemistryCombinatorial chemistryRutheniumAsymmetric Hydrogenation and CatalysisCatalysis for Biomass ConversionMesoporous Materials and Catalysis