Enantioselective reduction of aromatic ketones catalyzed by yeast cells in the presence of surfactants
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    Abstract:

    In aqueous buffer system containing surfactants (cetyltrimethyl ammonium bromide or sodium dodecyl sulfate or nonylphenol polyoxyethylene ether), the enantioselective reduction of 4’-chloroacetophenone to its corresponding chiral alcohol (S)-1-4’-chlorophenyl ethanol catalyzed by yeast cells were investigated. The results indicated that the conversion of 4’-chloroacetophenone was distinctly improved and the enantiomeric excess of product (S)-1-4’-chlorophenyl ethanol was barely changed when the surfactants were added to the system. Nonylphenol polyoxyethylene ether (NP-4) was the most appropriate additive among being added surfactants. In addition, the influence of nonionic surfactant NP-4 on the enantioselective reduction of aromatic ketones was studied. The results showed that the enantiomeric excesses of products (S)-1-aryl ethanol had little change and the conversions of all aromatic ketones were significantly enhanced in the presence of NP-4. It was also found that the increase of the substrate conversion was relevant to the electronic effect of the substituents on the aromatic ring. The stronger electron-donating capacity of the substituents was more beneficial to the increase of the substrate conversion.

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History
  • Received:January 07,2014
  • Revised:February 26,2014
  • Adopted:March 10,2014
  • Online: May 04,2014
  • Published:
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