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. 2012 Dec 7;14(23):5932-5.
doi: 10.1021/ol302848m. Epub 2012 Nov 19.

Cu(II)-catalyzed aerobic hydroperoxidation of Meldrum's acid derivatives and application in intramolecular oxidation: a conceptual blueprint for O2/H2 dihydroxylation

Scott W Krabbe  1 , Dung T Do, Jeffrey S Johnson
Affiliations

Cu(II)-catalyzed aerobic hydroperoxidation of Meldrum's acid derivatives and application in intramolecular oxidation: a conceptual blueprint for O2/H2 dihydroxylation

Scott W Krabbe et al. Org Lett. .

Abstract

Aerobic hydroperoxidation of Meldrum's acid derivatives via a Cu(II)-catalyzed process is presented. The mild reaction conditions are tolerant to pendant unsaturation allowing the formation of endoperoxides via electrophilic activation. Cleavage of the O-O bond provides 1,n-diols with differentiation of the hydroxy groups.

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Figures

Scheme 1
Scheme 1
Methods of Enolate Oxidation
Scheme 2
Scheme 2
Cu(II)-Catalyzed Aerobic Oxidation of a Substituted Meldrum’s Acid
Scheme 3
Scheme 3
Gold(I)-Catalyzed Endoperoxidation of Hydroperoxides and Endoperoxide Reactions
Scheme 4
Scheme 4
Iodoendoperoxidation of Homoallylhydroperoxy-Meldrum’s Acid and Barbituric Acid Derivatives
Scheme 5
Scheme 5
Endoperoxide Cleavage in 1,2-Dioxolane System
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