Enantioselektive Synthese von (1S,4R)-4-Hydroxycyclopent-2-enyl-acetat durch enzym-katalysierte Veresterung von cis-Cyclopent-2-en-1,4-diol mit Acetanhydrid. Gaschromatographische Untersuchungen zum Reaktionsmechanismus
DOI:
https://doi.org/10.2533/chimia.1991.195Abstract
(1S,4R)-4-Hydroxycyclopent-2-enyl-acetate (1), an attractive starting material for the synthesis of prostaglandins, was readily prepared by an enzyme-catalyzed interesterification procedure using acetic anhydride as acylation agent. As the chemical yield of the chiral monoacylation product is rather low (45%), we investigated the acylation mechanism of this reaction to optimize the product output. Kinetic measurements were carried out by means of gas chromatography on a chiral stationary phase, synthesized by methylation of β-cyclodextrin.
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1991-06-26
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Copyright (c) 1991 Swiss Chemical Society
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[1]
Chimia 1991, 45, 195, DOI: 10.2533/chimia.1991.195.