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

The oxidation of silyl enol ethers with MCPBA, known as the Rubottom oxidation, is an important method for the regioselective formation of α-hydroxyketones. Recent research in this area has been directed toward the search for alternative, more efficient oxidants to …

Review the Rubottom oxidation where the peroxyacid oxidation of silyl enol ether substrates is used to prepare the corresponding alpha-hydroxy carbonyl compounds.

2010年9月15日 · The transformation of a ketone into the corresponding α-hydroxyketone by means of the epoxidation or dihydroxylation of a silyl enolate of the ketone with m -chloroperbenzoic acid (m -CPBA) or dimethyldioxirane (DMDO) is generally referred to as the Rubottom reaction.

What is Rubottom Oxidation? The reaction of silyl enol ethers with the epoxidation reagent m-chloroperbenzoic acid (m-CPBA) and then rearranged and hydrolyzed to form α-hydroxy ketones. It is a method for α-hydroxylation of carbonyl compounds.

2023年2月1日 · A highly efficient catalytic asymmetric Rubottom-type oxidation is described. With meta -chloroperbenzoic acid ( m -CPBA) as the oxidant and chiral calcium phosphate as the catalyst, the facile transformation enables direct hydroxylation of N -Boc oxindoles and β-ketoesters in high yields (up to 99%) and in a highly enantioenriched fashion (up ...

2015年10月6日 · The epoxidation of silyl enol ethers with oxidants such as mCPBA and dioxirane leads to rearrangement into α-silyloxyketones. This reaction is used commonly to introduce a hydroxyl group to the α-position of ketones. ・ Brook, A. G.; Macrae, D. M. J. Organomet. Chem. 1974, 77, C19. doi: 10.1016/S0022-328X (00)81332-7.

2019年1月29日 · An aza analogue of the Rubottom oxidation is reported. This facile transformation takes place at ambient temperature and directly converts silyl enol ethers to the corresponding primary α-aminoketones. The use of hexafluoroisopropanol (HFIP) as the solvent is essential for the success of this reaction.

2014年1月1日 · α-Hydroxylation of enolsilanes. Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 15, 4319–4322. George Rubottom discovered the Rubottom oxidation when he was an assistant professor at the University of Puerto Rico. He is now a grant officer at the National Science Foundation.

Example 5, Double Rubottom oxidation 11 References 1. Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 15, 4319 4322. George Rubottom discovered the Rubottom oxidation when he was an assistant professor at the University of Puerto Rico. He is now a grant officer at the National Science Foundation. 2.