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Rubottom Oxidation

Rubottom oxidation   Named Reactions in Organic Synthesis
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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.

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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.


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