Preparation of Substituted 2 H -Pyrans via a Cascade Reaction from Methyl Coumalate and Activated Methylene Nucleophiles - Sorbonne Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2017

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

Abstract

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.
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Dates and versions

hal-01520277 , version 1 (10-05-2017)

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Liang Chang, Kristína Plevová, Serge Thorimbert, Luc Dechoux. Preparation of Substituted 2 H -Pyrans via a Cascade Reaction from Methyl Coumalate and Activated Methylene Nucleophiles. Journal of Organic Chemistry, 2017, 82 (10), pp.5499-5505. ⟨10.1021/acs.joc.7b00761⟩. ⟨hal-01520277⟩
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