The C/Si analogues 2-methyl-2-(3-methylbenzyl)but-3-en-1-ol ( 2a ) and (hydroxymethyl)methyl(3-methylbenzyl)vinylsilane ( 2b ) are chiral derivatives of the achiral fragrance materials majantol ( 1a ) and sila-majantol ( 1b ). Compounds 2a and 2b were synthesized as racemates, and the respective (+)- and (−)-enantiomers were obtained by chromatographic resolution (HPLC) of rac - 2a and rac - 2b using a chiral stationary phase. The enantiomerically pure compounds (+)- 2a, (−)- 2a, (+)- 2b, and (−)- 2b (optical rotations determined in methanol) were studied for their sensory properties. Both the odor character and the odor intensity of the silicon compounds (+)- 2b and (−)- 2b differ totally from those of the respective carbon analogues (+)- 2a and (−)- 2a .
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Schmid et al. (2003) studied this question.
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