Dynamic kinetic resolution over Cinchona-modified platinum catalyst: Hydrogenation of racemic ethyl 2-fluoroacetoacetate

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Abstract

The enantioselective hydrogenation over a Cinchona alkaloid-modified supported platinum catalyst and parallel spontaneous racemization under the reaction conditions of the unreacted enantiomer of ethyl 2-fluoroacetoacetate are described. Using the appropriate reaction conditions an 82% enantiomeric excess in favor of the (2S,3R)-ethyl 2-fluoro-3-hydroxybutanoate and a 99/1 threolerythro ratio were obtained. This novel method for producing optically enriched α-fluoro-β-hydroxy esters is the first example of dynamic kinetic resolution of a chirally labile racemic fluorinated compound over a modified heterogeneous metal catalyst carried out without using supplementary additives except the chiral modifier. The hydrogenation described here shows that the activation of the keto group of acetoacetates by one fluorine atom in the α position is also sufficient for obtaining high enantiomeric excess in the Orito reaction.

Original languageEnglish
Pages (from-to)515-522
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number4-5
DOIs
Publication statusPublished - Mar 1 2006

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Keywords

  • Cinchona alkaloids
  • Dynamic kinetic resolution
  • Enantioselectivity
  • Heterogeneous catalysis
  • Hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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