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 (https://doi.org/10.1016/S0957-4166(99)00446-2)

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.

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• Item metadata

  Item type:	Article
  ID code:	34213
  Dates:	Date Event 1999 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	20 Oct 2011 15:18
  Last modified:	08 Apr 2024 19:29
  URI:	https://strathprints.strath.ac.uk/id/eprint/34213