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Alkene Syn Dihydroxylation with Malonoyl Peroxides

James C. Griffith, Kevin M. Jones, Sylvain Picon, Michael J. Rawling, Benson M. Kariuki, Matthew Campbell and Nicholas C. O. Tomkinson*

*School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff CF10 3AT, U.K., Email: tomkinsonnccardiff.ac.uk

J. C. Griffith, K. M. Jones, S. Picon, M. J. Rawling, B. M. Kariuki, M. Campbell, N. C. O. Tomkinson, J. Am. Chem. Soc., 2010, 132, 14410-14411.

DOI: 10.1021/ja1066674 (free Supporting Information)


Abstract

Cyclopropyl malonoyl peroxide, which can be prepared in a single step from the commercially available diacid, enables an effective dihydroxylation of alkenes in the presence of water at 40C. Alkaline hydrolysis of the resulting monoester leads to the corresponding diol. With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity.


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Key Words

Dihydroxylation


ID: J48-Y2010-2930