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Issue 5, 2007
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Baeyer–Villiger oxidation of substituted cyclohexanones via lipase-mediated perhydrolysis utilizing ureahydrogen peroxide in ethyl acetate

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Abstract

A green method for Baeyer–Villiger oxidation based on the chemo-enzymatic perhydrolysis of carboxylic acids and esters has been optimized using Novozyme-435, the immobilized form of Candida antarctica lipase B, and the complex urea–hydrogen peroxide (UHP) in ethyl acetate. This protocol previously employed for the chemo-enzymatic epoxidation of unfunctionalized olefins was shown to be effective for the Baeyer–Villiger oxidation of cyclohexanone and substituted cyclohexanones. The absence of water in the reaction media avoided any hydrolysis of the oxidized product. A minimum amount of enzyme was necessary to show the catalytic effect. The reaction yields of substituted ε-caprolactones varied depending on the nature of the substituent.

Graphical abstract: Baeyer–Villiger oxidation of substituted cyclohexanones via lipase-mediated perhydrolysis utilizing urea–hydrogen peroxide in ethyl acetate

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Publication details

The article was received on 18 Dec 2006, accepted on 08 Feb 2007 and first published on 23 Feb 2007


Article type: Paper
DOI: 10.1039/B618175A
Citation: Green Chem., 2007,9, 459-462
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    Baeyer–Villiger oxidation of substituted cyclohexanones via lipase-mediated perhydrolysis utilizing ureahydrogen peroxide in ethyl acetate

    M. Y. Ríos, E. Salazar and H. F. Olivo, Green Chem., 2007, 9, 459
    DOI: 10.1039/B618175A

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