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

Cite this

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title = "The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)-trans-2-mercaptocyclohexanol and (-)-trans-2-mercaptocyclohexanol",
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.",
keywords = "meso-epoxides , homochiral thiols , cyclohexene oxide , lithium aluminum hydride",
author = "Harry Adams and Richard Bell and Yiu-Yin Cheung and Jones, {D. Neville} and Tomkinson, {Nicholas C. O.}",
year = "1999",
doi = "10.1016/S0957-4166(99)00446-2",
language = "Undefined/Unknown",
volume = "10",
pages = "4129--4142",
journal = "Tetrahedron: Asymmetry",
issn = "1362-511X",
number = "21",

}

The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)-trans-2-mercaptocyclohexanol and (-)-trans-2-mercaptocyclohexanol. / Adams, Harry; Bell, Richard; Cheung, Yiu-Yin; Jones, D. Neville; Tomkinson, Nicholas C. O.

In: Tetrahedron: Asymmetry, Vol. 10, No. 21, 1999, p. 4129-4142.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)-trans-2-mercaptocyclohexanol and (-)-trans-2-mercaptocyclohexanol

AU - Adams, Harry

AU - Bell, Richard

AU - Cheung, Yiu-Yin

AU - Jones, D. Neville

AU - Tomkinson, Nicholas C. O.

PY - 1999

Y1 - 1999

N2 - 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.

AB - 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.

KW - meso-epoxides

KW - homochiral thiols

KW - cyclohexene oxide

KW - lithium aluminum hydride

U2 - 10.1016/S0957-4166(99)00446-2

DO - 10.1016/S0957-4166(99)00446-2

M3 - Article

VL - 10

SP - 4129

EP - 4142

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

SN - 1362-511X

IS - 21

ER -