Homogeneous Asymmetric Catalysis in Fragrance Chemistry

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®, h...

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Bibliographic Details
Published in:Chemistry & biodiversity 2008-06, Vol.5 (6), p.1058-1069
Main Authors: Ciappa, Alessandra, Bovo, Sara, Bertoldini, Matteo, Scrivanti, Alberto, Matteoli, Ugo
Format: Article
Language:English
Subjects:
Asymmetric catalysis
Asymmetric catalysis, homogeneous
Catalysis
Chemistry, Organic - methods
Citralis
Citralis Nitrile
Enantioselective hydrogenation
Fixolide
homogeneous
Hydrogenation
Molecular Structure
Odorants - analysis
Perfume - chemistry
Phenoxanol
Stereoisomerism
Structure-Activity Relationship
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Summary: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.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.200890085