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

Frank Lewis, David Grayson

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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
Original languageEnglish
Pages (from-to)643-649
JournalTetrahedron Asymmetry
Volume23
Issue number9
DOIs
Publication statusPublished - 2012

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