Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines SAr.

Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines the nucleophilic aromatic substitution (SAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceeded DKR while higher barrier substrates proceeded KR.