Monatshefte für Chemie / Chemical Monthly

, Volume 134, Issue 8, pp 1151–1157

Lipase-catalyzed Irreversible Transesterification of Secondary Alcohols Using Isopropenyl Acetate


    • Organic Chemistry Department, University of Geneva, CH-12 Geneva 4, Switzerland
  • Volker SchurigRID="a"ID="a"&ensp;Dedicated to the Memory of Prof. <E5>E. Bayer</E5> 1927&ndash;2002
    • Institute of Organic Chemistry, University of Tübingen, D-72076 Tübingen, Germany

DOI: 10.1007/s00706-003-0025-1

Cite this article as:
Ghanem, A. & SchurigRID="a"ID="a" Dedicated to the Memory of Prof. E. Bayer 1927–2002, V. Monatshefte für Chemie (2003) 134: 1151. doi:10.1007/s00706-003-0025-1


 Asymmetric 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-β-Dex containing an undecamethylene spacer (C11-Chirasil-Dex).

Keywords. Enantiomeric resolution; Irreversible transesterification; Lipase; Secondary alcohols; Gas chromatography.
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© Springer-Verlag/Wien 2003