title: Direct synthesis of γ-pyrones by electrophilic condensation of β-ketoesters.
abstract: Triflic anhydride is a versatile electrophile that is able to activate poor nucleophiles. Herein, we show that readily available β-keto esters are activated by Tf2O furnishing γ-pyrones. Mechanistic studies suggest that this transformation proceeds via a double triflation, formation of an oxocarbenium intermediate and dealkylation promoted by a crucial nitrile additive.
authors.affiliation: University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090 Vienna, Austria. nuno.maulide@univie.ac.at and Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Catarina A B
authors.initials: CA
authors.lastname: Rodrigues
authors.affiliation: University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090 Vienna, Austria. nuno.maulide@univie.ac.at.
authors.forename: Antonio
authors.initials: A
authors.lastname: Misale
authors.affiliation: University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090 Vienna, Austria. nuno.maulide@univie.ac.at.
authors.forename: Florian
authors.initials: F
authors.lastname: Schiel
authors.affiliation: University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090 Vienna, Austria. nuno.maulide@univie.ac.at.
authors.forename: Nuno
authors.initials: N
authors.lastname: Maulide