Premium
Homogeneous Asymmetric Catalysis in Fragrance Chemistry
Author(s) -
Ciappa Alessandra,
Bovo Sara,
Bertoldini Matteo,
Scrivanti Alberto,
Matteoli Ugo
Publication year - 2008
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200890085
Subject(s) - chemistry , nitrile , stereocenter , enantiomer , homogeneous , olefin fiber , enantioselective synthesis , catalysis , organic chemistry , hydrocyanation , enantiomeric excess , kinetic resolution , combinatorial chemistry , thermodynamics , physics
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.