Oxidations with Dioxirane

Chemistry of Dioxiranes,
  Murray, R. W. Chem. Rev. 1989, 89, 1187
Dioxiranes: A New Class of Powerful Oxidants,
  Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
Dioxiranes: Oxidation Chemistry Made Easy,
  Adam, W.; Hadjiarapoglou, L. Top. Curr. Chem. 1993, 164, 45.
Dioxirane Oxidations: Taming the Reactivity-Selectivity Principle"
  Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-22.
The Development of Chiral, Nonracemic Dioxiranes for the Catalytic, Enantioselective Epoxidation of Alkenes
  Denmark, S. E.; Wu, Z. Synlett 1999, 847-59.
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
  Armstrong, A. Angew. Chem. Int. Ed. Engl. 2004, 43, 1460-2.
Organocatalytic Asymmetric Epoxidation of Olefins by Chiral Ketones
  Shi, Y. Acc. Chem Res. 2004, 37, 488-96.
Ketone-Catalyzed Asymmetric Epoxidation Reactions,
  Yang, D. Acc. Chem Res. 2004, 37, 497-505.

  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

Curci, R.; Fiorentino, M.; Troisi,L.; Edwards, J. O.; Pater, R. H. J. Org. Chem., 1980, 45, 4758–4760. Murray, R. W.; Jeyaraman, J. Org. Chem. 1985, 50, 2847. Murray, R. W.; Jeyaraman, R.; Mohan, L. Tetrahedron Lett. 1986, 27, 2335.

 

Preparation of Sensitive Epoxides:

 

Asymmetric Oxidations with Chiral Dioxiranes:

Tian, She, Shu, Yu, Shi J. Am. Chem. Soc. 2000, 122, 11551. Shi et al. J. Org. Chem. 1998, 63, 2948, 3099; Reviews: Denmark, S. E.; Wu, Z. Synlett, 1999, 847; Frohn, M.; Shi, Y. Synthesis 2000, 1979.

 

Glabrescol: Xiong, Z.; Corey, E.J. J. Am. Chem. Soc., 2000, 122, 9328-9329 DOI

 

Amine oxidations:

M. D. Wittman, S. J. Danishefsky, J. Org. Chem. 1990, 55, 1981.

 

Tertiary Hydrogen Abstraction

Bovicelli, P.; Lupattelli, P.; Mincione, E.; Prencipe, T; Curci, R. J. Org. Chem. 1992, 57, 5052.

 

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