Enantioselective and regioselective aza-Friedel-Crafts reaction of electron-rich phenols with isatin-derived ketimines.

ABSTRACT

An efficient asymmetric aza-Friedel-Crafts reaction of phenols with isatin-derived ketimines is described. The reaction, which was promoted by a Bi(OH)3/CPA system, gave a series of chiral 3-amino-2-oxindoles with high yields (up to 99%), excellent enantioselectivities (up to 99%) and moderate to very good regioselectivities (up to 25/1).