Premium
Lipase‐catalyzed irreversible transesterification of 1‐(2‐furyl)ethanol using isopropenyl acetate
Author(s) -
Ghanem Ashraf,
Schurig Volker
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/1520-636x(2001)13:2<118::aid-chir1007>3.0.co;2-q
Subject(s) - chemistry , transesterification , kinetic resolution , enantiomer , organic chemistry , ethanol , catalysis , alcohol , lipase , substrate (aquarium) , ethyl acetate , triacylglycerol lipase , methyl acetate , enantiomeric excess , enantioselective synthesis , chromatography , enzyme , oceanography , geology
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)‐β‐cyclodextrin. Chirality 13:118–123, 2001. © 2001 Wiley‐Liss, Inc.