The synthesis of (+)-trans-2-mercaptocyclohexanol and (-)-trans-2-mercaptocyclohexanol was described. Ring opening of cyclohexene oxide with (-)-4-methoxybenzyl-3(R)-nopanethiol followed by oxidn. gives two readily separable diastereomeric sulfoxides. These sulfoxides display very different thermal stability but both undergo regio-specific syn-elimination to give 1-cyclohexanol-2-sulfenic acid that can be treated in situ with 3,5-dimethylthiophenol to give a mixed disulfide. Redn. of these disulfides with lithium aluminum hydride gives the title compds. in enantiomerically pure form.
- homochiral thiols
- cyclohexene oxide
- lithium aluminum hydride
Adams, H., Bell, R., Cheung, Y-Y., Jones, D. N., & Tomkinson, N. C. O. (1999). The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)-trans-2-mercaptocyclohexanol and (-)-trans-2-mercaptocyclohexanol. Tetrahedron: Asymmetry, 10(21), 4129-4142. https://doi.org/10.1016/S0957-4166(99)00446-2