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Org Lett. 2012 Dec 21;14(24):6250-3. doi: 10.1021/ol3030154. Epub 2012 Nov 30.

Alkene dihydroxylation with malonoyl peroxides: catalysis using fluorinated alcohols.

Author information

  • 1School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK.

Abstract

The effect of fluorinated alcohols on the dihydroxylation of alkenes using cyclopropyl malonoyl peroxide is described. Addition of perfluoro-tert-butyl alcohol to a toluene solution of alkene and peroxide increases the rate of 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.

PMID:
23199002
[PubMed - indexed for MEDLINE]

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