Ru‐NHC‐Catalyzed Asymmetric Hydrogenation of 2‐Quinolones to Chiral 3,4‐Dihydro‐2‐Quinolones
Tianjiao Hu, Lukas Lückemeier, Constantin G. Daniliuc, Frank Glorius
Abstract
Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.
Topics & Concepts
Enantioselective synthesisCatalysisChemistryCombinatorial chemistryAsymmetric hydrogenationArylHalogenAlkylOptically activeOrganic chemistryAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisSurface Chemistry and Catalysis