Lipase-catalyzed irreversible transesterification of 1-(2-furyl)ethanol using isopropenyl acetate

A Ghanem; V Schurig

doi:10.1002/1520-636X(2001)13:2<118::AID-CHIR1007>3.0.CO;2-Q

Lipase-catalyzed irreversible transesterification of 1-(2-furyl)ethanol using isopropenyl acetate

Chirality. 2001 Feb;13(2):118-23. doi: 10.1002/1520-636X(2001)13:2<118::AID-CHIR1007>3.0.CO;2-Q.

Authors

A Ghanem¹, V Schurig

Affiliation

¹ Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany.

PMID: 11170255
DOI: 10.1002/1520-636X(2001)13:2<118::AID-CHIR1007>3.0.CO;2-Q

Abstract

Asymmetric acetylation of racemic 1-(2-furyl)ethanol with the innocuous acyl donor isopropenyl acetate catalyzed by lipases in organic media afforded the chiral alcohol and acetate in high enantiomeric excess (up to 99%). The effect of molecular sieves as well as organic solvents on the kinetic resolution were studied. An effective separation of the enantiomers of both substrate and product was performed using gas chromatography on the chiral stationary phase heptakis-(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin.