Kinetic Resolution of <scp>2‐Substituted</scp> 1,<scp>2‐Dihydroquinolines</scp> by <scp>Rhodium‐Catalyzed</scp> Asymmetric Hydroarylation<sup>†</sup>
Baohua Cai, Qingjing Yang, Ling Meng, Jun Wang
Abstract
Main observation and conclusion A highly efficient kinetic resolution of racemic 2‐substituted 1,2‐dihydroquinolines via Rh‐catalyzed asymmetric hydroarylation has been described for the first time. A variety of arylboronic acids coupled with 2‐substituted 1,2‐dihydroquinolines under mild reaction condition. The transformations into the enantio‐enriched 2,3‐diaryl‐tetrahydroquinolines as well as the recovered chiral 2‐aryl‐dihydroquinolines were obtained with high yields and excellent enantioselectivities (86%—99% ee , s factor up to 1057).
Topics & Concepts
ChemistryRhodiumCatalysisKinetic resolutionArylAsymmetric hydrogenationMedicinal chemistryResolution (logic)Combinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisAlkylArtificial intelligenceComputer scienceAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis