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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions
Romain Laher1, Christophe Marin2, Véronique Michelet1
1University Côte d'Azur, Institut de Chimie de Nice, UMR 7272 CNRS, Valrose Park, Faculty of Sciences, Nice 06108 CEDEX 2, France.
Abstract:
An efficient, and mild synthetic route for the preparation of functionalized volatile oxa-bicyclo[4.1.0]-hept-4-ene (29 compounds, 44-98% isolated yields) has been developed relying on the association of IPrAuCl with NaBArF. The remarkable selectivity was demonstrated on a 1 g and 25 g scale with low catalyst loadings. The synthetic utility of these low-molecular-weight enols was further demonstrated by the derivatization of some adducts and by the unprecedented olfactory evaluation of all bicyclic derivatives.
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