Lewis, Frank and Grayson, David (2012) The diastereoselective Meth-Cohn epoxidation of camphor-derived vinyl sulfones. Tetrahedron Asymmetry, 23 (9). pp. 643-649. ISSN 0957-4166
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Abstract
Some camphor-derived vinyl sulfones bearing oxygen functionality at the allylic position have been synthesized and their nucleophilic epoxidation reactions under Meth-Cohn conditions have been explored. The γ-oxygenated camphor-derived vinyl sulfones underwent mildly diastereoselective nucleophilic epoxidation reactions, affording the derived sulfonyloxiranes in up to 5.8:1 dr. The observed diastereoselectivities were sensitive to the reaction conditions employed. In contrast, no stereoselectivity was observed in the nucleophilic epoxidation of the corresponding γ-oxygenated isobornyl vinyl sulfone. A tentative mechanism has been proposed to explain the origins of the diastereoselectivity
| Item Type: | Article |
|---|---|
| Subjects: | F100 Chemistry |
| Department: | Faculties > Health and Life Sciences > Applied Sciences |
| Depositing User: | Frank Lewis |
| Date Deposited: | 02 Jan 2013 14:09 |
| Last Modified: | 17 Dec 2023 13:46 |
| URI: | https://nrl.northumbria.ac.uk/id/eprint/10887 |
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