Oxidations with Dioxirane
Chemistry of Dioxiranes,
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Dioxiranes: Oxidation Chemistry Made Easy,
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The Development of Chiral, Nonracemic Dioxiranes for the Catalytic, Enantioselective Epoxidation of Alkenes
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Chiral Ketone-Catalyzed Asymmetric Epoxidation of Olefins
Frohn, M.; Shi, Y. Synthesis 2000, 1979-2000.
Amine-Catalyzed Epoxidation of Alkenes: A New Mechanism for the Activation of Oxone
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Organocatalytic Asymmetric Epoxidation of Olefins by Chiral Ketones
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Ketone-Catalyzed Asymmetric Epoxidation Reactions,
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Dioxiranes are formed by the reaction of ketones with peroxy sulfate (Oxone™), and are usually generated in situ. They perform a variety of oxygen transfer reactions, usually to nucleophilic reagents, including epoxidation of double bonds, α-oxidation of enol silyl ethers, oxidation of amines to hydroxylamines and nitro compounds, oxidation of selenides to selenoxides, and sulfides to sulfoxides
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Preparation of Sensitive Epoxides:
Asymmetric Oxidations with Chiral Dioxiranes:
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Glabrescol: Xiong, Z.; Corey, E.J. J. Am. Chem. Soc., 2000, 122, 9328-9329 DOI
Amine oxidations:
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Tertiary Hydrogen Abstraction
Bovicelli, P.; Lupattelli, P.; Mincione, E.; Prencipe, T; Curci, R. J. Org. Chem. 1992, 57, 5052.
