Synthesis of α-oxygenated β, γ-unsaturated ketones by a catalytic rearrangement strategy. Issue 30 (18th July 2018)

• Record Type: Journal Article
• Authors: Lempenauer, Luisa; Soupart, Aline; Duñach, Elisabet; Lemière, Gilles
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 30(2018)
• Page Start: 5441
• Page End: 5445
• Publication Date: 2018-07-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01559g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A straightforward two-step entry to α-oxgenated β, γ-unsaturated ketones from readily available α, β-unsaturated ketones is disclosed. 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.