Homogeneous asymmetric catalysis in fragrance chemistry |
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Authors: | Ciappa Alessandra Bovo Sara Bertoldini Matteo Scrivanti Alberto Matteoli Ugo |
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Affiliation: | Dipartimento di Chimica, Università di Venezia, Calle Larga S. Marta, 2137, I-30123 Venice. alessandra.ciappa@nicosinternational.it |
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Abstract: | Opposite enantiomers of a chiral fragrance may exhibit different olfactory activities making a synthesis in high enantiomeric purity commercially and scientifically interesting. Accordingly, the asymmetric synthesis of four chiral odorants, Fixolide, Phenoxanol, Citralis, and Citralis Nitrile, has been investigated with the aim to develop practically feasible processes. In the devised synthetic schemes, the key step that leads to the formation of the stereogenic center is the homogeneous asymmetric hydrogenation of a prochiral olefin. By an appropriate choice of the catalyst and the reaction conditions, Phenoxanol, Citralis, and Citralis Nitrile were obtained in high enantiomeric purity, and odor profiles of the single enantiomers were determined. |
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Keywords: | Asymmetric catalysis, homogeneous Catalysis Enantioselective hydrogenation Fixolide® Phenoxanol® Citralis® Citralis Nitrile® |
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