Davis oxidation
In organic chemistry, the Davis oxidation is a reaction that allows for the generation of α-hydroxylated compounds from ketones or esters with the use of the Davis reagent (2-(phenylsulfonyl)-3-phenyloxaziridine) or other similar oxaziridine reagents.[1] The reaction is carried out in a basic environment to generate the corresponding enolate from the ketone or ester.
| Davis oxidation | |
|---|---|
| Named after | Franklin A. Davis |
| Reaction type | Organic redox reaction |
| Identifiers | |
| Organic Chemistry Portal | davis-oxidation |
Mechanism
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.
References
- 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.
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