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

Molecules

Hervé Rouillard¹  Emmanuel Deau¹  Lisianne Domon¹  Jean-René Chérouvrier¹  Marianne Graber¹ 

[1] Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France;

关键词: biocatalysis;    microwave irradiation;    lipase;    homochiral diols;    kinetic resolution;   

DOI  :  10.3390/molecules19079215

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.