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

Adams, Harry and Bell, Richard and Cheung, Yiu-Yin and Jones, D. Neville and Tomkinson, Nicholas C. O. (1999) The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)-trans-2-mercaptocyclohexanol and (-)-trans-2-mercaptocyclohexanol. Tetrahedron: Asymmetry, 10 (21). pp. 4129-4142. ISSN 0957-4166

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Abstract

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.