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Inverse-electron-demand Diels–Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyrones

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Abstract

Inverse-electron-demand Diels–Alder reactions of 3-electron-withdrawing group substituted α-pyrones with α,β-unsaturated hydrazones as electron-rich counterparts are catalyzed by Eu(hfc)3 to afford bicyclic lactone cycloadducts. This is an example of umpolung cycloaddition based on functional transformation of carbonyls to hydrazones. A subsequent dehydrazonation reaction enables indirect synthesis of carbonyl group-containing bicyclic lactones, which cannot be easily obtained by the cycloaddition of α-pyrones and enals.

Graphical abstract: Inverse-electron-demand Diels–Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyrones

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Publication details

The article was received on 30 Aug 2018, accepted on 02 Nov 2018 and first published on 05 Nov 2018


Article type: Communication
DOI: 10.1039/C8OB02132E
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Inverse-electron-demand Diels–Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyrones

    Y. Hashimoto, R. Abe, N. Morita and O. Tamura, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02132E

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