Alkene syn dihydroxylation with malonoyl peroxides

Griffith, James C and Jones, Kevin M and Picon, Sylvain and Rawling, Michael J and Kariuki, Benson M and Campbell, Matthew and Tomkinson, Nicholas C. O. (2010) Alkene syn dihydroxylation with malonoyl peroxides. Journal of the American Chemical Society, 132 (41). pp. 14409-14411. ISSN 0002-7863

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Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to >50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.