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Issue 3, 2017
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Direct synthesis of γ-pyrones by electrophilic condensation of β-ketoesters

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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.

Graphical abstract: Direct synthesis of γ-pyrones by electrophilic condensation of β-ketoesters

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Publication details

The article was received on 26 Aug 2016, accepted on 02 Dec 2016 and first published on 15 Dec 2016


Article type: Paper
DOI: 10.1039/C6OB01884J
Citation: Org. Biomol. Chem., 2017,15, 680-683
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    Direct synthesis of γ-pyrones by electrophilic condensation of β-ketoesters

    C. A. B. Rodrigues, A. Misale, F. Schiel and N. Maulide, Org. Biomol. Chem., 2017, 15, 680
    DOI: 10.1039/C6OB01884J

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