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

Org Biomol Chem. 2018 Aug 1;16(30):5441-5445. doi: 10.1039/c8ob01559g.

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.

Publication types

  • Research Support, Non-U.S. Gov't