A new chiral auxiliary in enantioselective hydrogenations: (-)-dihydrovinpocetine. Part I. Hydrogenation of isophorone

T. Tarnai, A. Tungler, T. Máthé, J. Petró, R. A. Sheldon, G. Tóth

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

A vinca-type synthetic alkaloid: (-)-dihydrovinpocetine is a promising chiral auxiliary in the enantioselective hydrogenation of the prochiral CC bond of isophorone. Various catalytic metals and supports have been screened. The effect of acidic additives is described. The highest optical yield (38%) is obtained with a Pd black catalyst. Mechanistic considerations and comparison with the known Pt/cinchona system have been made.

Original languageEnglish
Pages (from-to)41-47
Number of pages7
JournalJournal of Molecular Catalysis. A, Chemical
Volume102
Issue number1
DOIs
Publication statusPublished - Sep 6 1995

Keywords

  • Chiral auxiliary
  • Dihydrovinpocetine
  • Enantioselectivity
  • Hydrogenation
  • Isophorone

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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