Heterogeneous asymmetric reactions. 23. Enantioselective hydrogenation of ethyl pyruvate over cinchonine- and α-isocinchonine-modified platinum catalysts

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Abstract

The enantioselective hydrogenation of ethyl pyruvate to (S)-ethyl lactate over cinchonine- and α-isocinchonine-modified Pt/Al2O3 catalysts was studied as a function of modifier concentration and reaction temperature. The maximum enantioselectivities obtained under the applied mild conditions were 89% ee using cinchonine (0.014 mmol dm-3, 1 bar H2, 23 °C, 6% AcOH in toluene), and 76% ee in the case of α-isocinchonine (0.14 mmol dm-3, 1 bar H2 - 10°C, 69t AcOH in toluene). Since α-isocinchonine of rigid structure exists only in "anti-open" conformation these data provide additional experimental evidence to support the former suggestion concerning the dominating role of "anti-open" conformation in these cinchona-modified enantioselective hydrogenations.

Original languageEnglish
Pages (from-to)127-131
Number of pages5
JournalCatalysis Letters
Volume73
Issue number2-4
DOIs
Publication statusPublished - May 1 2001

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Keywords

  • Enantioselective
  • Ethyl pyruvate
  • Hydrogenation
  • Pt/AlO
  • α-isocinchonine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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