Issue 46, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
30 Aug 2018
Accepted
02 Nov 2018
First published
05 Nov 2018

Org. Biomol. Chem., 2018,16, 8913-8916

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, 16, 8913 DOI: 10.1039/C8OB02132E

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