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Lipase-catalyzed Irreversible Transesterification of Secondary Alcohols Using Isopropenyl Acetate
Authors:Ashraf Ghanem  Volker SchurigRID="a"ID="a"&ensp;Dedicated to the Memory of Prof <E>E Bayer</E> &ndash;
Institution:(1) Organic Chemistry Department, University of Geneva, CH-12 Geneva 4, Switzerland, CH;(2) Institute of Organic Chemistry, University of Tübingen, D-72076 Tübingen, Germany, DE
Abstract:Summary. enspAsymmetric acetylation of a set of secondary alcohols with the innocuous acyl donor isopropenyl acetate catalyzed by a lipase from Pseudomonas cepacia immobilized on ceramic particles (PSL-C) in toluene as organic medium afforded the chiral alcohols and the corresponding acetates in high enantiomeric excess (up to 99%). An effective baseline separation of the enantiomers of both substrate and product was performed in one analysis without derivatization using gas chromatography on a new chiral stationary phase (CSP) Chirasil-beta-Dex containing an undecamethylene spacer (C11-Chirasil-Dex).Received November 27, 2002; accepted (revised) January 9, 2003 Published online June 2, 2003
Keywords:, Enantiomeric resolution, Irreversible transesterification, Lipase, Secondary alcohols, Gas chromatography,
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