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A Domino Ring-Opening/Epoxidation of 1,2-Dioxines

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posted on 2004-04-02, 00:00 authored by Ben W. Greatrex, Dennis K. Taylor, Edward R. T. Tiekink
When allowed to react with alkaline hydrogen peroxide, monocyclic 1,2-dioxines ring-open to their isomeric γ-hydroxyenone intermediates which are rapidly epoxidized to afford trans-4-hydroxy-2,3-epoxyketones in 21−81% yield. In the case of meso-1,2-dioxines, Co(II) complex catalyzed asymmetric ring-opening of the 1,2-dioxine may be employed to furnish enantioenriched epoxides