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

Authors

  • Alexander Knoll
  • Monika Böhme
  • Steffen Merker
  • Gerd Fabian
  • Barbara Häfner
  • Fritz Theil

DOI:

https://doi.org/10.2533/chimia.1991.195

Abstract

(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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Published

1991-06-26