Synthesis and olfactory evaluation of allylic α‐quaternary ether ketones. (16th December 2018)

• Record Type: Journal Article
• Authors: Lempenauer, Luisa; Soupart, Aline; Lemière, Gilles; Duñach, Elisabet
• Is Part Of: Flavour and fragrance journal. Volume 34:Number 2(2019:Mar.)
• Page Start: 90
• Page End: 103
• Publication Date: 2018-12-16
• Subjects: catalysis -- enol ethers -- odour evaluation -- semipinacol rearrangement -- unsaturated ether ketones; Flavor -- Periodicals; Odors -- Periodicals; Smell -- Periodicals; 668.54
• DOI: 10.1002/ffj.3481
• Languages: English
• ISSNs: 0882-5734

Abstract

Abstract: Unprecedented α‐oxygenated β, γ‐unsaturated ketones bearing a quaternary carbon at the α‐position were synthesized in two steps from readily available α, β‐unsaturated ketones. The compounds were prepared on a gram scale under mild conditions via a key rearrangement step catalysed by 1 mol% of p ‐toluenesulfonic acid as a low‐priced and sustainable catalyst. The olfactory properties of this novel family of odorants as well as of some derivatives have been assessed, revealing a quite broad odour spectrum and a pronounced susceptibility of the olfactory properties towards structural changes. Abstract : Olfactory properties of a series of new compounds issued from an acid‐catalysed rearrangement of 2‐oxa diallylic alcohols.