Lipase-catalyzed Irreversible Transesterification of Secondary Alcohols Using Isopropenyl Acetate

Ashraf Ghanem, Volker Schurig

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)1151-1157
Number of pages7
JournalMonatshefte fur Chemie
Volume134
Issue number8
DOIs
Publication statusPublished - 1 Aug 2003
Externally publishedYes

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Transesterification
Lipase
Alcohols
Acetylation
Enantiomers
Toluene
Gas chromatography
Acetates
Substrates
Chirasil-Dex
isopropenyl acetate

Cite this

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abstract = "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, Gas chromatography, Irreversible transesterification, Lipase, Secondary alcohols",
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Lipase-catalyzed Irreversible Transesterification of Secondary Alcohols Using Isopropenyl Acetate. / Ghanem, Ashraf; Schurig, Volker.

In: Monatshefte fur Chemie, Vol. 134, No. 8, 01.08.2003, p. 1151-1157.

Research output: Contribution to journalArticle

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AU - Schurig, Volker

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KW - Enantiomeric resolution

KW - Gas chromatography

KW - Irreversible transesterification

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