Article · Wikipedia archive · Last revised Jul 9, 2026

Davis oxidation

In organic chemistry, the Davis oxidation or Davis' oxaziridine oxidation refers to oxidations involving the use of the Davis reagent or other similar oxaziridine reagents. This reaction mainly refers to the generation of α-hydroxy carbonyl compounds (acyloins) from ketones or esters. The reaction is carried out in a basic environment to generate the corresponding enolate from the ketone or ester. This reaction has been shown to work for amides.

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Davis oxidation
Named after Franklin A. Davis
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal davis-oxidation

In organic chemistry, the Davis oxidation or Davis' oxaziridine oxidation refers to oxidations involving the use of the Davis reagent (2-(phenylsulfonyl)-3-phenyloxaziridine) or other similar oxaziridine reagents.1 This reaction mainly refers to the generation of α-hydroxy carbonyl compounds (acyloins) from ketones or esters.23 The reaction is carried out in a basic environment to generate the corresponding enolate from the ketone or ester. This reaction has been shown to work for amides.4

Other oxidations carried out by Davis' reagent include the oxidation of sulfides and selenides to sulfoxides56 and selenoxides7 without further oxidation; the oxidation of alkenes to epoxides;8910 and the oxidation of amines to hydroxylamines and amine oxides.11

Mechanism

Regarding the α-hydroxylation of carbonyls, the base first converts the ketone or ester into its corresponding enolate. Then, the enolate anion as a nucleophile attacks the oxygen atom of the oxaziridine in a SN2 mechanism, forming a hemiaminal intermediate. The intermediate then fragments into a sulfinimine, and, after protonation, the desired α-hydroxyketone or α-hydroxyester.31213

See also

See also

References

References

  1. Kürti, László; Czakó, Barbara (29 September 2005). Strategic Applications of Named Reactions in Organic Synthesis. Elsevier Science. pp. 130–131. ISBN 978-0-12-429785-2.
  2. Davis, Franklin A.; Vishwakarma, Lal C.; Billmers, Joanne G.; Finn, John (1 August 1984). "Synthesis of α-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines". The Journal of Organic Chemistry. 49 (17): 3241–3243. doi:10.1021/jo00191a048.
  3. Davis, Franklin A.; Chen, Bang Chi (1992). "Asymmetric hydroxylation of enolates with N-sulfonyloxaziridines". Chemical Reviews. 92 (5): 919–934. doi:10.1021/cr00013a008.
  4. Evans, David Albert; Morrissey, Michael M.; Dorow, Roberta L. (1985-07-01). "Asymmetric oxygenation of chiral imide enolates. A general approach to the synthesis of enantiomerically pure α-hydroxy carboxylic acid synthons". Journal of the American Chemical Society. 107 (14): 4346–4348. doi:10.1021/ja00300a054.
  5. Mata, Ernesto G. (1996). "Recent advances in the synthesis of sulfoxides from sulfides". Phosphorus, Sulfur, and Silicon and the Related Elements. 117 (1): 231–286. doi:10.1080/10426509608038790.
  6. Bohé, Luis; Lusinchi, Marie; Lusinchi, Xavier (1999). "Oxygen atom transfer from a chiral N-alkyl oxaziridine promoted by acid. The asymmetric oxidation of sulfides to sulfoxides". Tetrahedron. 55 (1): 155–156. doi:10.1016/S0040-4020(98)01035-7.
  7. Davis, Franklin A.; Stringer, Orum D.; Billmers, Joanne M. (1983). "Oxidation of selenides to selenoxides using 2-sulfonyloxaziridines". Tetrahedron Letters. 24 (12): 1213–1216. doi:10.1016/S0040-4039(00)81617-2.
  8. Davis, Franklin A.; Abdul-Malik, Nadia F.; Awad, Sami B.; Harakal, Mark E. (1981). "Epoxidation of olefins by oxaziridines". Tetrahedron Letters. 22 (10): 917–920. doi:10.1016/0040-4039(81)89008-9.
  9. Davis, Franklin A.; Harakal, Mark E.; Awad, Sami B. (1983). "Chemistry of oxaziridines. 4. Asymmetric epoxidation of unfunctionalized alkenes using chiral 2-sulfonyloxaziridines: evidence for a planar transition state geometry". Journal of the American Chemical Society. 105 (10): 3123–3126. doi:10.1021/ja00348a029.
  10. Bohé, Luis; Lusinchi, Marie; Lusinchi, Xavier (1999). "Oxygen atom transfer from a chiral oxaziridinium salt. Asymmetric epoxidation of unfunctionalized olefins". Tetrahedron. 55 (1): 141–154. doi:10.1016/S0040-4020(98)01034-5.
  11. Zajac, Walter W. Jr.; Walters, Thomas R.; Darcy, Michael G. (1988). "Oxidation of amines with 2-sulfonyloxaziridines (Davis' reagents)". The Journal of Organic Chemistry. 53 (25): 5856–5860. doi:10.1021/jo00260a012.
  12. Davis, Franklin A.; Sheppard, Aurelia C.; Chen, Bang Chi; Haque, M. Serajul (1990). "Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl)oxaziridine". Journal of the American Chemical Society. 112 (18): 6679–6690. doi:10.1021/ja00174a035.
  13. Davis, Franklin A.; Weismiller, Michael C.; Murphy, Christopher K.; Reddy, R. Thimma; Chen, Bang Chi (1992). "Chemistry of oxaziridines. 18. Synthesis and enantioselective oxidations of the [(8,8-dihalocamphoryl)sulfonyl]oxaziridines". The Journal of Organic Chemistry. 57 (26): 7274–7285. doi:10.1021/jo00052a050.