Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

One-Pot Synthesis of α-Carbonyl Bicyclic Furans via a Sequential Diels–Alder/5-Exo-Dig Cyclization/Oxidation Reaction

One-Pot Synthesis of α-Carbonyl Bicyclic Furans via a Sequential Diels–Alder/5-Exo-Dig Cyclization/Oxidation Reaction
Wesley A. Chalifoux, Khagendra B. Hamal
A new one-pot approach to construct α-carbonyl bicyclic furans from easily accessible diynones is described. This reaction sequence proceeds via a Diels–Alder cycloaddition reaction catalyzed by dimethylaluminum chloride followed by a 5-exo-dig cyclization/oxidation reaction catalyzed by copper(II) chloride. This methodology generates α-carbonyl-functionalized dihydroisobenzofuran derivatives in good to excellent yields.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02479

DOI: 10.1021/acs.joc.7b02479

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