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

This reaction has been shown to work for amides.[2]

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
  1. 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.
  2. 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.