Monatshefte für Chemie / Chemical Monthly

, Volume 134, Issue 8, pp 1151–1157 | Cite as

Lipase-catalyzed Irreversible Transesterification of Secondary Alcohols Using Isopropenyl Acetate

  • Ashraf Ghanem
  • Volker SchurigRID="a"ID="a"&ensp;Dedicated to the Memory of Prof. <E5>E. Bayer</E5> 1927&ndash;2002

Summary.

 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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Copyright information

© Springer-Verlag/Wien 2003

Authors and Affiliations

  • Ashraf Ghanem
    • 1
  • Volker SchurigRID="a"ID="a"&ensp;Dedicated to the Memory of Prof. <E5>E. Bayer</E5> 1927&ndash;2002
    • 2
  1. 1.Organic Chemistry Department, University of Geneva, CH-12 Geneva 4, SwitzerlandCH
  2. 2.Institute of Organic Chemistry, University of Tübingen, D-72076 Tübingen, GermanyDE

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