Enzymic resolution of 2-substituted cyclohexanols through lipase-mediated esterification

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• 作者：Wimmer ; Zden??k ; Skouridou ; Vasso ; Zarev??cka ; Marie ; ??aman ; David ; Kolisis ; Fragiskos N.
• 刊名：Tetrahedron: Asymmetry
• 出版年：2004
• 出版时间：December 13, 2004
• 年：2004
• 卷：15
• 期：24
• 页码：3911-3917
• 全文大小：366 K

文摘

Several lipases were used for the kinetic resolution of the racemic cis- and trans-isomers of 2-(4-methoxybenzyl)cyclohexanol, by lipase-mediated esterification of the substrates to the corresponding acetate isomers. Conversion of the products and the remaining deracemized substrates into diastereoisomeric esters of 3,3,3-trifluoromethyl-2-methoxy-2-phenylpropanoic acid, their analysis by chiral HPLC and assignment of their absolute configurations through their ¹H and ¹⁹F NMR spectra, were the basis of evaluation of the studied enzymic process. Lipase from Rhizomucor miehei (RML) was found to be the most efficient enzyme regarding enantiomeric excess (ee) and yield of the desired products, while resolution by lipase from Rhizopus arrhizus (RAL) resulted in satisfactory ee and lower yields.