Marked deuterium isotope effects on the enantioselectivity in rhodium-catalyzed asymmetric hydrogenation of enamides

Tsuneo Imamoto, Takuma Itoh, Kazuhiro Yoshida, Ilya D. Gridnev

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Deuterium isotope effects on the enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of enamides and related substrates have been studied. Distinct deuterium isotope effects were observed in the hydrogenation of aryl-substituted enamides having an ortho substituent that is capable of forming a hydrogen bond. The observed isotope effects are interpreted in terms of the competitive reactions of two dihydride intermediates and dideuteride intermediates that exist in equilibrium in the catalytic cycle.

Original languageEnglish
Pages (from-to)1636-1641
Number of pages6
JournalChemistry - An Asian Journal
Volume3
Issue number8-9
DOIs
Publication statusPublished - 2008 Sep 1
Externally publishedYes

Keywords

  • Asymmetric hydrogenation
  • Deuterium
  • Enamides
  • Isotope effects
  • Rhodium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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