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)
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 40°C. 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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