Synthesis 2021; 53(21): 4020-4029
Oxygen-Tethered 1,6-Enynes and [4.1.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry
Romain Laher
a
Institut de Chimie de Nice, University Côte d’Azur, UMR 7272 CNRS, Valrose Park, Faculty of Sciences, Nice 06108 CEDEX 2, France
,
Emilie Gentilini
a
Institut de Chimie de Nice, University Côte d’Azur, UMR 7272 CNRS, Valrose Park, Faculty of Sciences, Nice 06108 CEDEX 2, France
,
Christophe Marin
b
Expressions Parfumées, 136 chemin de St Marc, Grasse 06130, France
,
a
Institut de Chimie de Nice, University Côte d’Azur, UMR 7272 CNRS, Valrose Park, Faculty of Sciences, Nice 06108 CEDEX 2, France
› Author Affiliations This work was supported by the Centre National de la Recherche Scientifique (CNRS) and the University Côte d’Azur. We gratefully acknowledge Expressions Parfumées for a grant to R.L.. This study was partly supported by research funding from the Canceropôle PACA, Institut National du Cancer, and Région Sud.
Abstract
The synthesis of original structures for the fragrance industry bearing bicyclic scaffolds is described. To the best of our knowledge, these structures are not found in the fragrance industry, neither from natural nor synthetic pathways. NHC–gold-type catalysts showed excellent activities leading to light bicyclic enol ethers. Several bicyclic adducts were prepared in good to excellent yields (18–99%). Evaluation of NHC–Au complexes allowed to reach a TOF of 300 h–1 . The evaluation for the organoleptic properties of [4.1.0]-bicyclic ethers were compared with the unprecedented properties of the 1,6-enyne precursors. Evaluations of starting materials showed a great interest in these structures with various olfactory facets. In this study, we depicted the similarity and differences between starting ethers and their cycloisomerized bicyclic counterparts.
Key words
gold catalysis -
N-heterocyclic carbenes -
fragrance -
1,6-enynes -
bicyclic compounds
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-1526-7917.
Supporting Information
Publication History
Received: 12 May 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
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