title: Microwave-assisted kinetic resolution of homochiral (Z)-cyclooct-5-ene-1,2-diol and (Z)-2-acetoxycyclooct-4-enyl acetate using lipases.
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.
authors.affiliation: Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France. herve.rouillard@univ-lr.fr.
authors.forename: Hervé
authors.initials: H
authors.lastname: Rouillard
authors.affiliation: Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France. emmanuel.deau@univ-orleans.fr.
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Deau
authors.affiliation: Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France. lisianne.domon@univ-lr.fr.
authors.forename: Lisianne
authors.initials: L
authors.lastname: Domon
authors.affiliation: Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France. jcherouv@univ-lr.fr.
authors.forename: Jean-René
authors.initials: JR
authors.lastname: Chérouvrier
authors.affiliation: Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France. marianne.graber@univ-lr.fr.
authors.forename: Marianne
authors.initials: M
authors.lastname: Graber
authors.affiliation: Université de La Rochelle, UMR CNRS 7266 LIENSs, Avenue Crépeau, La Rochelle 17042, France. valerie.thiery@univ-lr.fr.
authors.forename: Valérie
authors.initials: V
authors.lastname: Thiéry
mesh_terms: D000085:Acetates / Q000302:isolation & purification*; D000107:Acetylation; D001426:Bacterial Proteins / Q000737:chemistry; D055162:Biocatalysis; D034242:Cyclooctanes / Q000302:isolation & purification*; D004800:Enzymes, Immobilized / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D005656:Fungal Proteins / Q000737:chemistry; D006018:Glycols / Q000302:isolation & purification*; D006868:Hydrolysis; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D008872:Microwaves; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D001426:Bacterial Proteins; D034242:Cyclooctanes; D004800:Enzymes, Immobilized; D004852:Epoxy Compounds; D005656:Fungal Proteins; D006018:Glycols; D008049:Lipase