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Alkene Dihydroxylation with Malonoyl Peroxides: Catalysis Using Fluorinated Alcohols

Sylvain Picon, Michael Rawling, Matthew Campbell and Nicholas C. O. Tomkinson*

*WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, U.K., Email: Nicholas.Tomkinsonstrath.ac.uk

S. Picon, M. Rawling, M. Campbell, N. C. O. Tomkinson, Org. Lett., 2012, 14, 6250-6253.

DOI: 10.1021/ol3030154 (free Supporting Information)


Abstract

Addition of perfluoro-tert-butyl alcohol to a toluene solution of alkene and cyclopropyl malonoyl peroxide increases the rate of dihydroxylation product formation and the stereoselectivity observed, providing a simple and effective method for acceleration of this important class of reaction. Basic hydrolysis of the crude reaction mixture provides access to syn-diols in high yield and stereoselectivity.

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Key Words

Dihydroxylation, Peroxy Acids


ID: J54-Y2012-3890