Asymmetric hydrogenation of racemic 2-fluorocyclohexanone over cinchona modified Pt/Al2O3 catalyst

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Abstract

The first example of enantioselective heterogeneous catalytic hydrogenation of an α-fluoro ketone is reported. The hydrogenation of racemic 2-fluorocyclohexanone over cinchonidine- or methoxycinchonidine-modified Pt/Al2O3 resulted in diastereoselective and enantioselective formation of the cis-(1 R, 2 S)-2-fluorocyclohexanol. Due to the preferential hydrogenation of the S enantiomer, the kinetic resolution of the substrate was possible; the unreacted R enantiomer was accumulated in the reaction mixture. Under our experimental conditions, high diastereoselectivities (up to 85%) and good enantioselectivities (up to 59%) were obtained, demonstrating that activation of a ketone by a single α fluorine atom is efficient for obtaining enantiodiscrimination in this heterogeneous catalytic system.

Original languageEnglish
Pages (from-to)255-259
Number of pages5
JournalJournal of Catalysis
Volume244
Issue number2
DOIs
Publication statusPublished - Dec 10 2006

Keywords

  • Cinchona alkaloid
  • Enantioselectivity
  • Fluoroketone
  • Heterogeneous hydrogenation
  • Kinetic resolution
  • Platinum catalyst

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

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