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
Full text not available in this repository. (Request a copy from the Strathclyde author)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.
| Item type: | Article |
|---|---|
| ID code: | 34213 |
| Notes: | M1 - Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved. CAPLUS AN 1999:784702(Journal) |
| Keywords: | meso-epoxides , homochiral thiols , cyclohexene oxide , lithium aluminum hydride, Chemistry |
| Subjects: | Science > Chemistry |
| Department: | Faculty of Science > Pure and Applied Chemistry |
| Related URLs: | |
| Depositing user: | Pure Administrator |
| Date Deposited: | 20 Oct 2011 16:18 |
| Last modified: | 12 Mar 2012 11:35 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/34213 |
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