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Silylating Reagents: A Powerful Tool for the Construction of Isosteric Analogs of Highly Branched Odorants
Author(s) -
Doszczak Leszek,
Gasperi Tecla,
SaintDizier Alexandre,
Loreto M. Antonietta,
Enders Dieter
Publication year - 2004
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.200490147
Subject(s) - chemistry , odor , silylation , acetaldehyde , organoleptic , derivatization , reagent , organosilicon , terpene , flavor , organic chemistry , stereochemistry , high performance liquid chromatography , food science , catalysis , ethanol
We have discovered that α ‐[dimethyl(thexyl)silyl]acetaldehyde (=[dimethyl(1,1,2‐trimethylpropyl)silyl]acetaldehyde; 31 ) has a strong, woody odor. Structural analysis has shown resemblance to known odorants with similar organoleptic properties. On the basis of structureodor relationships, new and more‐powerful woody and ambery sila odorants were prepared. Further derivatization led to a set of compounds with very interesting organoleptic properties. Selected chiral compounds were also prepared stereoselectively. The influence of the absolute configuration on the olfactory properties was in agreement with theoretical assumptions. We also designed other groups of organosilicon odorants. The compounds discovered can be obtained in a few simple steps from commercially available reagents, and may find application in the fragrance and flavor industry. Their structures provide interesting data for further research on structureodor relationships.