Enzymatic resolution of 2-dialkylaminomethylcyclopentanols and -cycloheptanols |
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| Affiliation: | 1. Departamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Carrera 30 No. 45-03, Bogotá, Colombia;2. Departamento de Ciencias Básicas, Universidad ECCI, Sede Bogotá, Carrera 19 No. 49-20, Bogotá, Colombia;3. Crystallography and Chemistry of Materials, CrisQuimMat, Department of Chemistry, Universidad de los Andes, Carrera 1 No. 18A-10, Bogotá 111711, Colombia |
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| Abstract: | Extensive lipase screening was performed in relation to the asymmetric acetylation of rac-2-dialkylaminomethylcyclanols 1–5. The lipase PS- and Novozym 435-catalysed resolutions of compounds 1–5 were based on asymmetric acylation of the secondary OH group at the R-stereogenic centre with various vinyl esters, in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as acylating agent, with diethyl ether or with diisopropyl ether as solvent. The reaction rates were markedly affected by the size of the alicyclic ring, and by the solvent. |
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