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Molecules 2014, 19(7), 9215-9227; doi:10.3390/molecules19079215

Microwave-Assisted Kinetic Resolution of Homochiral (Z)-Cyclooct-5-ene-1,2-diol and (Z)-2-Acetoxycyclooct-4-enyl Acetate Using Lipases

Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France
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Received: 30 May 2014 / Revised: 21 June 2014 / Accepted: 30 June 2014 / Published: 2 July 2014
(This article belongs to the Special Issue ECSOC-17)
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Abstract

Over the last decade, the use of biocatalysts has become an attractive alternative to conventional chemical methods, especially for organic synthesis, due to their unusual properties. Among these enzymes, lipases are the most widely used, because they are cheap, easily available, cofactor-free, and have broad substrate specificity. Combined to microwave heating in non-aqueous medium, recent results suggest that irradiation may influence the enzyme activity. This Communication reports the benefits of lipases and the microwave irradiation on the kinetic resolution of racemic homochiral (Z)-cyclooct-5-ene-1,2-diol and (Z)-2-acetoxycyclooct-4-enyl acetate. In order to best achieve the kinetic resolution, different parameters were studied including the type of lipase, the temperature, the impact of microwave power compared to conventional heating. Optimization of the reaction parameters lead to the obtainment of highly enriched or enantiopure diols and diesters in a clean, efficient and safe way. View Full-Text
Keywords: biocatalysis; microwave irradiation; lipase; homochiral diols; kinetic resolution biocatalysis; microwave irradiation; lipase; homochiral diols; kinetic resolution
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Rouillard, H.; Deau, E.; Domon, L.; Chérouvrier, J.-R.; Graber, M.; Thiéry, V. Microwave-Assisted Kinetic Resolution of Homochiral (Z)-Cyclooct-5-ene-1,2-diol and (Z)-2-Acetoxycyclooct-4-enyl Acetate Using Lipases. Molecules 2014, 19, 9215-9227.

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