The electronic effect of ligands on stereoselectivity in the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction under a carbon monoxide atmosphere

Dong Eun Kim, Choong Choi, In Su Kim, Séverine Jeulin, Virginie Ratovelomanana-Vidal, Jean Pierre Genêt, Nakcheol Jeong

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Based on the proposed mechanism, the electronic effects of various ligands on the stereoselectivity and reaction rate of the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction were examined. We demonstrated that both the reaction rate and the enantioselectivity are significantly dependent on the electron density of the ligands; when ligands bearing deshielded phosphine were utilized, the reaction rate was slower, but the products were obtained with improved enantioselectivity.

Original languageEnglish
Pages (from-to)4053-4059
Number of pages7
JournalSynthesis
Issue number23
DOIs
Publication statusPublished - 2006 Dec 1

Keywords

  • Asymmetric catalysts
  • Atropisomeric ligands
  • BINAP ligands
  • Electronic effects
  • Pauson-Khand reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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