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

Harry Adams, Richard Bell, Yiu-Yin Cheung, D. Neville Jones, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

34 Citations (Scopus)

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.
Original languageUndefined/Unknown
Pages (from-to)4129-4142
Number of pages14
JournalTetrahedron: Asymmetry
Volume10
Issue number21
DOIs
Publication statusPublished - 1999

Keywords

  • meso-epoxides
  • homochiral thiols
  • cyclohexene oxide
  • lithium aluminum hydride

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