257950-77-9Relevant academic research and scientific papers
The cleavage of meso-epoxides with homochiral thiols: Synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol
Adams, Harry,Bell, Richard,Cheung, Yiu-Yin,Jones, D. Neville,Tomkinson, Nicholas C.O.
, p. 4129 - 4142 (2007/10/03)
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 sulfoxides. These sulfoxides display very different thermal stability but both undergo regio-specific syn-elimination to give cyclohexan- 1-ol-2-sulfenic acid that can be reacted in situ with 3,5-dimethylthiophenol to give a mixed disulfide. Reduction of these disulfides with lithium aluminium hydride gives the title compounds in enantiomerically pure form.
