A chiral Bronsted acid-catalyzed highly enantioselective Mannich-type reaction of -diazo esters with in situ generated N-acyl ketimines

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of -diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based -amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.