Heterogeneous asymmetric reactions, 14. Epicinchona alkaloids in the enantioselective hydrogenation of ethyl pyruvate over Pt/alumina. What determines the sense of enantioselection?

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Abstract

The enantioselective hydrogenation of ethyl pyruvate to (R)- and (S)-ethyl lactate over Pt/Al2O3 catalyst was investigated using epiquinine (42% ee) and cpiquinidine (22% ee) as modifiers and the results were compared with those found for quinine (85% ee) and quinidine (81% ee). The experimental results show that the sense of enantioselection is determined by the conformation of the entire alkaloid, and the structure of the intermediate is a 1:1 complex of the pyruvate and the 'anti open' conformer of the cinchona alkaloid.

Original languageEnglish
Pages (from-to)371-377
Number of pages7
JournalReaction Kinetics and Catalysis Letters
Volume68
Issue number2
DOIs
Publication statusPublished - Jan 1 1999

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Keywords

  • Enantioselective
  • Epicinchona alkaloids
  • Ethyl pyruvate
  • Hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

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