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Synthesis of α-oxygenated β,γ-unsaturated ketones by a catalytic rearrangement strategy

Abstract

A straightforward two-step entry to α-oxgenated β,γ-unsaturated ketones from readily available α,β-unsaturated ketones is dis-closed. It was found that bis(allylic) alcohols undergo a skeletal re-arrangement in the presence of 1 mol% of cheap and non-corrosive p-toluenesulfonic acid. Computational studies were con-ducted to support the mechanism and to rationalise the influence of the catalyst acidity on the product selectivity.

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Publication details

The article was accepted on 09 Jul 2018 and first published on 11 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01559G
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Synthesis of α-oxygenated β,γ-unsaturated ketones by a catalytic rearrangement strategy

    L. Lempenauer, A. Soupart, E. Dunach and G. Lemière, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB01559G

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