Synthesis p. 540 - 541 (1988)
Update date:2022-08-10
Topics:
Theil, Fritz
Ballschuh, Sibylle
Schick, Hans
Haupt, Monika
Haefner, Barbara
Schwarz, Sigfrid
(1S,4R)-(-)-4-Hydroxy-2-cyclopentenyl acetate (2), a versatile intermediate in prostaglandin syntheses, was readily prepared by an efficient enzyme-catalyzed enantioselective monoacetylation of cis-2-cyclopenten-1,4-diol (1) with 2,2,2-trichloroethyl acetate in the organic solvent system triethylamine/tetrahydrofuran.The chemical yield reached nearly 50percent.The enantiomeric excess of the crude product was 95percent.It could be raised to more than 99percent by a single recrystalization.Commercially available pancreatin, a crude enzyme preparation from porcine pancreas, was used as biocatalyst.
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