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

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Abstract

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

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

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Publication details

The article was received on 14 May 2018, accepted on 09 Jul 2018 and first published on 11 Jul 2018


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

    L. Lempenauer, A. Soupart, E. Duñach and G. Lemière, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01559G

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