Multicomponent condensation reactions via ortho-Quinone Methides
Files
Accepted manuscript
Date
2017-04-07
Authors
Allen, Emily E.
Zhu, Calvin
Panek, James S.
Schaus, Scott E.
Version
Accepted manuscript
OA Version
Citation
E.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.7b00647
Abstract
Iron(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.