Allen, Emily E.Zhu, CalvinPanek, James S.Schaus, Scott E.2024-02-292024-02-292017-04-07E.E. Allen, C. Zhu, J.S. Panek, S.E. Schaus. 2017. "Multicomponent Condensation Reactions via ortho-Quinone Methides" Organic Letters, Volume 19, Issue 7, pp.1878-1881. https://doi.org/10.1021/acs.orglett.7b006471523-70601523-7052https://hdl.handle.net/2144/48261Iron(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo Diels-Alder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered while investigating a two-component strategy using 2-(hydroxy(phenyl)methyl)phenols to access the desired ortho-quinone methide in a Diels-Alder condensation. The two-component condensation also afforded the corresponding benzopyran products in yields up to 97%. Taken together, the two- and three-component strategies using ortho-quinone methide intermediates provide efficient access to benzopyrans in good yields and selectivities.1878-1881Print-ElectronicScience & technologyPhysical sciencesChemistry, organicChemistryRobustadial ADiastereoselective synthesisBiomimetic synthesisChiral biphenolsFormal synthesisAcidCycloadditionsElectrophileDerivativesCyclizationChemical sciencesOrganic chemistryArticle10.1021/acs.orglett.7b006470000-0002-5733-2511 (Panek, James S)189625