Enantioselective and Z/E-selective conjugate addition of α-substituted cyanoacetates to acetylenic esters catalyzed by bifunctional ruthenium and iridium complexes

Yasuharu Hasegawa, Ilya D. Gridnev, Takao Ikariya

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Metal-based catalysts: The title reaction provided the chiral adducts in high yields, excellent enantiomeric excess, and high Z/E selectivity. A combined NMR/DFT study revealed a key intermediate for the stereoselective reaction and a possible reaction mechanism (see the optimized transition-state structure).

Original languageEnglish
Pages (from-to)8157-8160
Number of pages4
JournalAngewandte Chemie - International Edition
Volume49
Issue number44
DOIs
Publication statusPublished - 2010 Oct 25
Externally publishedYes

Keywords

  • Acetylenic esters
  • Asymmetric conjugate addition
  • Bifunctional catalysts
  • Density functional calculations
  • Ruthenium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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