4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 45, Pages 9261-9267

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob02054k

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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 pi-pi interactions between the phenyl ring on phosphoric acid and quinolinone play important roles in the enantioselectivity.

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