Related Reactions
Davis Oxidation
Prilezhaev Reaction
Synthesis of α-hydroxy ketones
Rubottom Oxidation
The synthesis of α-hydroxy ketones is achieved by reaction of silyl enol ethers with mCPBA, with subsequent rearrangement. Aqueous work up or reaction with TBAF (fluoride ions) gives the desired product after desilylation
Mechanism of the Rubottom Oxidation
The enol ether double bond is epoxidized by the peracid. Relief of the epoxide ring strain drives the rearrangement with migration of the silyl group to give the silylated α-hydroxy ketone product.
Recent Literature
Aza-Rubottom Oxidation: Synthetic Access to Primary α-Aminoketones
Z. Zhou, Q.-Q. Cheng, L. K�rti, J. Am. Chem. Soc.,
2019,
141, 2242-2246.
Oxidation of Methyl Trimethylsilyl Ketene Acetals to α-Hydroxyesters with
Urea Hydrogen Peroxide Catalyzed by Methyltrioxorhenium
S. Stanković, J. H. Espenson, J. Org. Chem., 2000,
65, 5528-5530.
