Lipase-catalyzed enantiotope selective acetylation of 2-acyloxypropane- 1,3-diols. Influence of the acyl moiety on the selectivity

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Abstract

Preparation and lipase-catalyzed enantiotope selective acetylation of the prochiral 2-acyloxypropane-1,3-diols (1a-h) including sulfonic ester (1a- c) and carboxylic ester (1d-h) series is described. A strong influence of the acyl moiety in these diols on the enantiotope selectivity of the porcine pancreatic lipase (PPL)-catalyzed reaction with vinyl acetate was observed. The best results were achieved with the 2-(4-methylbenzoyl)oxy- and cyclohexanecarbonyloxypropane-1,3-diols (1g and 1h) resulting in acetylated products (2g) of ≥ 98% e.e. in 77% yield and (2h) of 95% e.e. in 66% yield, respectively. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)583-596
Number of pages14
JournalJournal of Molecular Catalysis - B Enzymatic
Volume10
Issue number6
DOIs
Publication statusPublished - Nov 1 2000

Keywords

  • Acylation
  • Enantioselection
  • Enzymes and enzyme reactions
  • Substituent effects

ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

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