The diastereoselective Meth-Cohn epoxidation of camphor-derived vinyl sulfones

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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Official URL: http://dx.doi.org/10.1016/j.tetasy.2012.04.014

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 > School of Life Sciences > Applied Sciences
Depositing User: Frank Lewis
Date Deposited: 02 Jan 2013 14:09
Last Modified: 18 May 2017 04:34
URI: http://nrl.northumbria.ac.uk/id/eprint/10887

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