Issue 5, 2007
From the journal:

Green Chemistry

Baeyer–Villiger oxidation of substituted cyclohexanonesvia lipase-mediated perhydrolysis utilizing urea–hydrogen peroxide in ethyl acetate†

María Yolanda Ríos,a   Enrique Salazara  and  Horacio F. Olivo*a  

* Corresponding authors

a Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa, USA
E-mail: horacio-olivo@uiowa.edu
Fax: +1 (319) 335 8766
Tel: +1 (319) 335 8849

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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Article information

DOI
https://doi.org/10.1039/B618175A
Article type
Paper
Submitted
18 Dec 2006
Accepted
08 Feb 2007
First published
23 Feb 2007

Green Chem., 2007,9, 459-462

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Baeyer–Villiger oxidation of substituted cyclohexanones via lipase-mediated perhydrolysis utilizing urea–hydrogen 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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