Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Preparation of Substituted 2H-Pyrans via a Cascade Reaction from Methyl Coumalate and Activated Methylene Nucleophiles

Preparation of Substituted 2H-Pyrans via a Cascade Reaction from Methyl Coumalate and Activated Methylene Nucleophiles
Luc Dechoux, Liang Chang, Serge Thorimbert, Kristína Plevová
The reaction of methyl coumalate with a wide range of methylene active compounds, such as keto-esters or keto-sulfones and cyclic or acyclic diketones, afforded more than 30 2,3,5,6-tetrasubstituted 2H-pyrans. The reaction proceeds via a cascade reaction involving a Michael addition-6π-electrocyclic ring opening-proton transfer and 6π electrocyclization, in which a variety of functional groups were tolerated.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00761

DOI: 10.1021/acs.joc.7b00761

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