3-Mercapto-2-methylpentanol, a new powerful flavor compound, exhibits two stereocenters giving rise to two pairs of diastereomers. To determine differences in the sensory properties, all four diastereomers and enantiomers were stereo- and enantioselectively synthesized. A highly diastereoselective aldol reaction using a chiral auxiliary was one of the key steps in the synthesis. Further derivatization yielded the enantiopure compounds. Odor thresholds in air and water were determined.
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Lüntzel et al. (2000) studied this question.
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