Enantioselectivity of Pseudomonas cepacia lipase for the acetylation of 2-hydroxy carboxylic acid esters

Structurally different ethyl or methyl 2-hydroxy carboxylates were resolved by Pseudomonas cepacia lipase-catalysed acetylations with vinyl acetate in diethylether. One type of the alcoholic substrates (2-hydroxy-2-arylacetates and 2-hydroxy-3-arylpropinates) contained a HO-group at the stereocentre...

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Bibliographic Details
Published inACH, models in chemistry Vol. 135; no. 4; pp. 625 - 640
Main Authors Sundholm, O, Kanerva, LT
Format Journal Article
LanguageEnglish
Published BUDAPEST Akademiai Kiado 01.01.1998
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
(R)-CYANOHYDRINS
CATALYSIS
CYANOHYDRINS
ORGANIC-SOLVENTS
ACYLATION
RESOLUTION
DERIVATIVES
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Summary:Structurally different ethyl or methyl 2-hydroxy carboxylates were resolved by Pseudomonas cepacia lipase-catalysed acetylations with vinyl acetate in diethylether. One type of the alcoholic substrates (2-hydroxy-2-arylacetates and 2-hydroxy-3-arylpropinates) contained a HO-group at the stereocentre. These compounds were resolved with high enantioselectivity (ee 91-->99) at ca. 50% conversion. The other alcoholic substrates ((threo-2-hydroxy-3-methylbutyrate and threo- or erythro-2-hydroxy-3-aryl-3-arylthio(or aryloxy)propionates) with two stereocentres generally resulted in enantiopure products and the reactions stopped at 50% conversion.
ISSN:1217-8969