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When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions

Romain Laher, Christophe Marin and Véronique Michelet*

*University Côte d’Azur, Institut de Chimie de Nice, UMR 7272 CNRS, Valrose Park, Faculty of Sciences, Nice 06108 CEDEX 2, France, Email: veronique.micheletuniv-cotedazur.fr

R. Laher, C. Marin, V. Michelet, Org. Lett., 2020, 22, 4058-4062.

DOI: 10.1021/acs.orglett.0c00843


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Abstract

The combination of IPrAuCl and NaBArF catalyzes an efficient synthesis of functionalized volatile oxa-bicyclo[4.1.0]-hept-4-ene compounds in good yields. The utility of these low-molecular-weight enols was demonstrated by derivatization of some adducts and olfactory evaluation.


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Key Words

3,4-dihydro-2H-pyrans


ID: J54-Y2020