Copper-catalyzed asymmetric 1,2-arylboration of enamines: access to chiral borate-containing 3,3′-disubstituted isoindolinones

Abstract

An enantioselective copper-catalyzed 1,2-arylboration reaction of enamines has been developed by employing (R)-xyl-BINAP as a chiral ligand. A number of chiral borate-containing 3,3′-disubstituted isoindolinones were obtained in moderate to good yields and good to excellent enantioselectivities from the reactions of N-(o-iodobenzoyl)enamines and bis(pinacolato)diboron (B₂pin₂) under mild reaction conditions. Synthetic transformations of the products were conducted to demonstrate the practicality of this reaction.