Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines

A highly enantioselective addition o hydroxyquinolines to isatin-derived ketimines hasbeen realized using a quinine-derived thiourea organocatalyst. The reaction affords chiral 3-amino-2-oxindoles bearing a quinoline moiety with a quaternary stereocenter in high yields (up to 98%) and excellent enantioselectivities (up to 99%). Moreover, we can extend this methodology for the enantioselective functionalization of 5-hydroxyisoquinoline. This methodology represents, to the best of our knowledge, the first enantioselective addition of hydroxyquinolines to imines