Heterocycles 32. Efficient kinetic resolution of 1-(2-arylthiazol-4-yl)ethanols and their acetates using lipase B from Candida antarctica

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• 作者：Denisa Hap?u ; J¨¹rgen Brem ; M?d?lina Mois? ; Monica-Ioana To?a ; Florin Dan Irimie ; Valentin Zaharia
• 关键词：Biocatalysis ; Kinetic resolution ; Thiazole ; Chiral secondary alcohols
• 刊名：Journal of Molecular Catalysis B: Enzymatic
• 出版年：2013
• 出版时间：October, 2013
• 年：2013
• 卷：94
• 期：Complete
• 页码：88-94
• 全文大小：573 K

文摘

In this paper we describe the chemoenzymatic synthesis of new enantiomerically enriched (R)- and (S)-1-(2-arylthiazol-4-yl)ethanols and their acetates by enzymatic enantioselective acetylation of the racemic alcohols rac-2a-d and by methanolysis of the corresponding racemic esters rac-3a-d mediated by lipase B from Candida antarctica (CaL-B) in non-aqueous media. In terms of stereoselectivity and activity, both procedures, acylation and alcoholysis, gave similar good results (50 % conversion, E ? 200). The absolute configuration of the kinetic resolution products was determined by a detailed ¹H NMR study of the Mosher's derivatives of (S)-2b.