Enantioselective hydrogenation of α-β-unsaturated ketones

A. Tungler, M. Kajtar, T. Mathe, G. Toth, E. Fogassy, J. Petro

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

In the asymmetric synthesis of chiral compounds the reduction of prochiral unsaturated reactants has a great importance. The use of proline as a chiral agent in hydrogenations, where the proline is applied as homogeneous chiral catalyst in ring-closure reactions of triketones, was reported previously. In this paper Proline is used in the hydrogenations of α-β unsaturated ketones or acetophenone with palladium on carbon catalysts, producing saturated ketones or α-phenyl-ethyl-alcohol of 5-60% optical purity. The influence of parameters on optical yield is also investigated. UV, NMR and circular dichroism measurements allow to propose the following mechanism: the zwitterionic form of proline gives a Schiff-base or enamin with the ketones; in the hydrogenation of this compound asymmetric induction takes place, which results in optically active ketones after hydrolizing the saturated product.

Original languageEnglish
Pages (from-to)159-171
Number of pages13
JournalCatalysis Today
Volume5
Issue number2
DOIs
Publication statusPublished - Apr 1989

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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