Chiral phosphoric acid-catalyzed enantioselective synthesis of functionalized pyrrolinones containing a geminal diamine core via an aza-Friedel–Crafts reaction of newly developed pyrrolinone ketimines

Abstract

A class of novel pyrrolinone ketimines was used in the catalytic asymmetric aza-Friedel–Crafts reaction with phenolic compounds for the first time. Under the catalysis of a chiral phosphoric acid catalyst, various functionalized pyrrolinone derivatives bearing a geminal diamine core were constructed in good to excellent yields (up to 99%) with high enantioselectivities (up to 99% ee). The scale-up reaction and further transformations of the product also demonstrated the potential application of this protocol.