Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids

This manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted γ -pyrones from β -ketoacids. The reaction proceeds in the presence of trifluoromethanesulfonic anhydride via an unprecedented decarboxylative auto-condensation of the starting material. Herein, the scope and limitat...

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Published inMonatshefte für Chemie Vol. 148; no. 1; pp. 57 - 62
Main Authors Merad, Jérémy, Maier, Thomas, Rodrigues, Catarina A. B., Maulide, Nuno
Format Journal Article
LanguageEnglish
Published Vienna Springer Vienna 01.01.2017
Springer Nature
Springer Nature B.V
Subjects
Analytical Chemistry
Aromatic compounds
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Condensates
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Physical Sciences
Science & Technology
Theoretical and Computational Chemistry
Decarboxylative condensation
Pyrones
Heterocyclic chemistry
Ketoacids
Convergent synthesis
Electrophilic activation
ETHERS
gamma-Pyrones
NATURAL-PRODUCTS
beta-Ketoacids
REARRANGEMENTS
AMIDES
β-Ketoacids
γ-Pyrones
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Summary:This manuscript describes the convergent synthesis of aryl- and alkyl-disubstituted γ -pyrones from β -ketoacids. The reaction proceeds in the presence of trifluoromethanesulfonic anhydride via an unprecedented decarboxylative auto-condensation of the starting material. Herein, the scope and limitations of this transformation are reported. Graphical abstract
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ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-016-1851-2