Enantioselective Syntheses and Sensory Properties of 2-Methyl-tetrahydrofuran-3-thiol Acetates

The enantioselective synthesis of four stereoisomers of 2-methyl-tetrahydrofuran-3-thiol acetate was achieved. The two enantiomers of the important intermediate cis-2-methyl-3-hydroxy-tetrahydrofuran were obtained by Sharpless asymmetric dihydroxylation (AD), whereas the two enantiomers of trans-2-methyl-3-hydroxy-tetrahydrofuran were derived from the corresponding optically active cis-isomers by Mitsunobu reaction. Each stereoisomer of 2-methyl-3-hydroxy-tetrahydrofuran went through mesylation and nucleophilic substitution to afford the corresponding product with specific configuration. (2R,3S)- and (2R,3R)-2-methyl-tetrahydrofuran-3-thiol acetate were obtained in 80% ee, whereas the (2S,3R)- and (2S,3S)-isomers were in 62% ee. The odor properties of the synthesized four stereoisomers were evaluated by gas chromatography-olfactometry (GC-O), which revealed perceptible differences among stereoisomers both in odor features and in intensities.