Application of ionic liquids in enzymic resolution by hydrolysis of cycloalkyl acetates

A comparative study was performed in the enzymic resolution of the isomers of 2-(4-methoxybenzyl)cyclohexyl acetates 1 and 2. The investigation consisted in application of three commercially available lipases (Novozyme 435, Lipozyme IM and non-immobilized powdered lipase from Candida antarctica), tw...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Xanthakis, Epameinondas, Zarevúcka, Marie, Šaman, David, Wimmerová, Martina, Kolisis, Fragiskos N., Wimmer, Zdeněk
Format: Article in Journal/Newspaper
Language:English
Published: 2006
Subjects:
1 Butyl 4 methylpyridinium chloride
1,3 Dimethylimidazolinium methylsulfate
2 (4 methoxybenzyl)cyclohexanol
Acetic acid derivative
Cyclohexanol derivative
Ionic liquid
Triacylglycerol lipase
Chemical Sciences
Natural Sciences
Antarc*
Antarctica
Online Access:https://hdl.handle.net/10488/27524
https://doi.org/10.1016/j.tetasy.2006.10.045
https://api.elsevier.com/content/abstract/scopus_id/33845270633
Description
Summary:A comparative study was performed in the enzymic resolution of the isomers of 2-(4-methoxybenzyl)cyclohexyl acetates 1 and 2. The investigation consisted in application of three commercially available lipases (Novozyme 435, Lipozyme IM and non-immobilized powdered lipase from Candida antarctica), two ionic liquids (1-butyl-4-methylpyridinium chloride and 1,3-dimethylimidazolinium methyl sulfate), three modifications of the reaction conditions and two respective isomers of the racemic substrate (1 and 2), and resulted in our finding the appropriate conditions to get both of the products, stereoisomers of 2-(4-methoxybenzyl)cyclohexanol (3; 1S,2S) or (5; 1S,2R), and (in some cases) also the stereoisomers of the deracemized substrate (4; 1R,2R) or (6; 1R,2S) with high or acceptable enantiomeric purity.

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