{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["13(40)"],"submitter":["Stegbauer S"],"pubmed_abstract":["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 AlBr<sub>3</sub>-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."],"journal":["Chemical science"],"pagination":["11856-11862"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9580482"],"repository":["biostudies-literature"],"pubmed_title":["Chiral Lewis acid catalysis in a visible light-triggered cycloaddition/rearrangement cascade."],"pmcid":["PMC9580482"],"pubmed_authors":["Jandl C","Stegbauer S","Bach T"],"additional_accession":[]},"is_claimable":false,"name":"Chiral Lewis acid catalysis in a visible light-triggered cycloaddition/rearrangement cascade.","description":"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 AlBr<sub>3</sub>-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.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Oct","modification":"2025-04-05T13:27:47.549Z","creation":"2025-04-05T13:27:47.549Z"},"accession":"S-EPMC9580482","cross_references":{"pubmed":["36320923"],"doi":["10.1039/d2sc03159k"]}}