A catalytic enantioselective method for the synthesis of chiral 1H-isoindoles bearing quaternary stereogenic centers is reported. Powered by readily accessible phosphordiamidite ligands, the presented palladium(0)-catalyzed C-H function-alization uses trifluoroacetimidoyl chlorides as electrophilic components. It delivers previously inaccessible perfluoroalky-lated 1H-isoindoles in high yields and enantioselectivities. The subsequent diastereoselective addition of nucleophiles provides access to densely substituted and sterically hindered isoindolines.