Substituent position-driven reaction pathways in the heterogeneous one-pot reduction/asymmetric hydrogenation of nitro-substituted (E)-2,3- diphenylpropenoic acids over Pd catalyst

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Abstract

The reaction pathway in the heterogeneous enantioselective hydrogenation of nitro-substituted (E)-2,3-diphenylpropenoic acids over Pd catalyst modified by cinchonidine is determined by the position of the substituent. The reaction route was indicated by the H 2 consumption curve and enantioselectivity of the final amino acid or 3-phenyl-1,2,3,4-tetrahydro-2- quinolone formed by intramolecular amidation. The obtained enantioselectivities were low with the exception of acids bearing nitro substituent in para position on the 3-phenyl moiety, the latter resulting in good, up to 80 % optical purity. The present study is the first to report the enantioselective heterogeneous catalytic preparation of 1,2,3,4-tetrahydro-2-quinolones and presents an attractive method for obtaining optically enriched 3-(4-aminophenyl)-2- phenylpropionic acids.

Original languageEnglish
Pages (from-to)16-27
Number of pages12
JournalArkivoc
Volume2012
Issue number5
Publication statusPublished - Jan 16 2012

Keywords

  • 2-quinolone
  • Amino acid
  • Cinchonidine
  • Enantioselective hydrogenation
  • Heterogeneous catalyst
  • Nitro substituent
  • Palladium
  • Unsaturated carboxylic acid

ASJC Scopus subject areas

  • Organic Chemistry

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