The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol

The synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol is described. Ring opening of cyclohexene oxide with (-)-4-methoxybenzylnopan-3(R)-thiol 1a followed by oxidation gives two readily separable diastereomeric sulfox ides. These sulfoxides display very different thermal stability but both un dergo regio-specific syn-elimination to give cyclohexan-1-ol-2-sulfenic aci d that can be reacted in situ with 3,5-dimethylthiophenol to give a mixed d isulfide. Reduction of these disulfides with lithium aluminium hydride give s the title compounds in enantiomerically pure form. (C) 1999 Elsevier Scie nce Ltd. All rights reserved.