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Synthesis of α-oxygenated β,γ-unsaturated ketones by a catalytic rearrangement strategy.
Organic & Biomolecular Chemistry 2018 August 2
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.
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