Silylating Reagents: A Powerful Tool for the Construction of Isosteric Analogs of Highly Branched Odorants

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 structure-odor 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 structure-odor relationships. © Verlag Helvetica Chimica Acta, Postfach, CH-8042 Zürich, Switzerland, 2005