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Enantiopure Chiral Derivatives of the Fragrance Materials Majantol and Sila-majantol: A Bioisosteric Carbon/Silicon Switch with Drastic Effects on the Sensory Characteristics
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2003
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Asymmetric CatalysisBioisosteric Carbon/silicon SwitchDerivativesEnantiopure Chiral DerivativesChiral DerivativesPure CompoundsOrganic ChemistryStereoselective SynthesisChemistryFragrance Materials MajantolPharmacologyChiral Stationary PhaseChemical DerivativeEnantioselective Synthesis
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.