Enantioselective intramolecular [2 + 2] photocycloaddition using phosphoric acid as a chiral template

Abstract

The enantioselective intramolecular [2 + 2] photocycloaddition of 4-bishomoally-2-quinolone (quinolinone) using phosphoric acid as a chiral template has been developed. Mechanistic studies using several NMR measurement techniques and density functional theory (DFT) calculations indicate that π–π interactions between the phenyl ring on phosphoric acid and quinolinone play important roles in the enantioselectivity.