Stereochemistry of the enantioselective reductive alkylation of proline with ketones

Gábor Tóth, Attila Kovács, Tibor Tarnai, Antal Tungler

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Abstract

Enantioselective heterogeneous catalytic hydrogenation of pyruvic acid ethyl ester and benzylidene-acetone with Pd/C catalyst in the presence of (S)-proline was investigated, where the reductive alkylation of proline was observed. The structure of the main products was elucidated by different NMR methods and the configuration and predominant conformation of (-)-(S)-1-(1-Ethoxycarbonyl-ethyl)-pyrrolidine-(S)-2-carboxylic acid (1) was established.

Original languageEnglish
Pages (from-to)331-338
Number of pages8
JournalTetrahedron: Asymmetry
Volume4
Issue number3
DOIs
Publication statusPublished - Mar 1993

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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