Enantioselective intramolecular [2 + 2] photocycloaddition using phosphoric acid as a chiral template
Ryukichi Takagi, Chihiro Tabuchi
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.
Topics & Concepts
ChemistryPhosphoric acidIntramolecular forceEnantioselective synthesisRing (chemistry)Optically activeDensity functional theoryCombinatorial chemistryComputational chemistryStereochemistryOrganic chemistryCatalysisOxidative Organic Chemistry ReactionsOrganic Chemistry Cycloaddition ReactionsRadical Photochemical Reactions