biostudies-literatureUnknown13(40)Stegbauer SCascade (domino) reactions facilitate the formation of complex molecules from simple starting materials in a single operation. It was found that 1-naphthaldehyde derivatives can be converted to enantioenriched (82-96% <i>ee</i>) polycyclic benzoisochromenes <i>via</i> a cascade of <i>ortho</i> photocycloaddition and ensuing acid-catalysed rearrangement reactions. The cascade was initiated by irradiation with visible light (<i>λ</i> = 457 nm) and catalysed by a chiral AlBr₃-activated 1,3,2-oxazaborolidine (14 examples, 65-93% yield). The absolute configuration of the products was elucidated by single crystal X-ray crystallography. Mechanistic experiments suggest that the <i>ortho</i> photocycloaddition occurs on the triplet hypersurface and that the chiral catalyst induces in this step the observed enantioselectivity.Chemical science11856-11862https://www.ebi.ac.uk/biostudies/studies/S-EPMC9580482biostudies-literatureChiral Lewis acid catalysis in a visible light-triggered cycloaddition/rearrangement cascade.PMC9580482Jandl CStegbauer SBach TfalseChiral Lewis acid catalysis in a visible light-triggered cycloaddition/rearrangement cascade.Cascade (domino) reactions facilitate the formation of complex molecules from simple starting materials in a single operation. It was found that 1-naphthaldehyde derivatives can be converted to enantioenriched (82-96% <i>ee</i>) polycyclic benzoisochromenes <i>via</i> a cascade of <i>ortho</i> photocycloaddition and ensuing acid-catalysed rearrangement reactions. The cascade was initiated by irradiation with visible light (<i>λ</i> = 457 nm) and catalysed by a chiral AlBr₃-activated 1,3,2-oxazaborolidine (14 examples, 65-93% yield). The absolute configuration of the products was elucidated by single crystal X-ray crystallography. Mechanistic experiments suggest that the <i>ortho</i> photocycloaddition occurs on the triplet hypersurface and that the chiral catalyst induces in this step the observed enantioselectivity.2022-01-01T00:00:00Z2022 Oct2025-04-05T13:27:47.549Z2025-04-05T13:27:47.549ZS-EPMC95804823632092310.1039/d2sc03159k