Enantioselective hydrogenation of exocyclic α,β-unsaturated ketones part II. Hydrogenation in the presence of (S)-proline

Gabriella Fogassy, Antal Tungler, Albert Lévai, Gábor Tóth

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27 Citations (Scopus)

Abstract

In the asymmetric synthesis of chiral compounds, the reduction of prochiral unsaturated reactants has a great importance. (S)-proline as a chiral auxiliary is used in the hydrogenations of exocyclic α,β-unsaturated ketones with palladium on carbon catalysts, producing the corresponding saturated ketones with an optical purity up to 20%. The influence of the parameters (solvents, additives) on the optical yield is also investigated. The highest enantioselectivity was obtained in ethyl acetate and acetonitrile (ee 20%), at atmospheric pressure and room temperature.

Original languageEnglish
Pages (from-to)101-106
Number of pages6
JournalJournal of Molecular Catalysis A: Chemical
Volume179
Issue number1-2
DOIs
Publication statusPublished - Feb 18 2002

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Keywords

  • (E)-2-benzylidene-1-benzosuberone
  • (S)-proline
  • Enantiomeric excess
  • Enantioselective hydrogenation
  • Exocyclic α,β-unsaturated
  • Palladium catalyst

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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