Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

Rubottom Oxidation

Rubottom oxidation   Named Reactions in Organic Synthesis
Reaction category:
Oxidation

Other featured reactions:

In 1974 G.M. Rubottom, A.G. Brook and A. Hassner independently created a method to prepare alpha-hydroxy aldehydes and ketones through the oxidation of their silyl enol ethers using meta-chloro peroxy benzoic acid (mCPBA). Today the peroxyacid oxidation of silyl enol ether substrates to prepare the corresponding alpha-hydroxy carbonyl compounds is known as the Rubottom oxidation. Synthesis of the potent anti-thrombotic (+/-)rishirilide B utilized the Rubottom oxidation, as did the synthesis of the antitumour antibiotic FR901464.




Which is your favorite named reaction?   Vote now


Find your reagents and pack sizes

 

Other reaction categories:

Pericyclic and photochemical reactions NEW!

Radical reactions

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle formation

Transition metal-catalyzed couplings

Reactions involving carbonyl compounds

Reduction reactions

Rearrangement reactions

Electrophilic addition reactions




Some relevant Alfa Aesar products for the Rubottom oxidation:

3-Chloroperoxybenzoic acid, 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water
Chlorotrimethylsilane, 98%
Trimethylsilyl trifluoromethanesulfonate, 99%
Lithium Diisopropylamide, 28% (2.2M) in THF/n-heptane, packaged under Argon in resealable septum cap bottles
Triethylamine, 99+% Triethylamine, 99+%

We have many ketones and aldehyde building blocks as useful precursors to the silyl enol ether substrates.

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware