Catalytic enantioselective reactions by the chiral cobalt complexes as Lewis acid catalysts

Satoko Kezuka, Tsuyoshi Mita, Izumi Iwakura, Taketo Ikeno, Tohru Yamada

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

This article is focused on the chiral Lewis acid catalyses by the optically active ketoiminato-cobalt complexes. Screening of the central metal of the ketoiminato complex catalysts for the enantioselective hetero Diels-Alder reaction revealed that cobalt was the most effective for affording the corresponding pyranone derivatives. The corresponding cationic cobalt(III) complexes were developed as an efficient Lewis acid catalyst and subjected to the hetero Diels-Alder reaction and the carbonyl-ene reaction. It was found that their counter anions significantly influenced the reactivity and the enantioselectivity in the carbonyl-ene reaction. The cationic cobalt(III) complexes could be employed as the efficient catalysts for the enantioselective 1, 3-dipolar cycloaddition reaction. Because of the competitive coordination of the nitrone, the 1, 3-dipolar cycloaddition with the monodentate α, β-unsaturated aldehyde has been limited to several catalyses, although these cationic cobalt(III) complexes effectively catalyzed the reaction to afford the isoxazoline derivative with high-to-excellent stereoselectivities. These types of cobalt complex catalysts could be applied to the enantioselective Henry reaction even in the presence of amine bases, and the enantioselective chemical fixation of carbon dioxide to obtain the optically active cyclic carbonate.

Original languageEnglish
Pages (from-to)604-615
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume63
Issue number6
DOIs
Publication statusPublished - 2005 Jun

Keywords

  • 1, 3-dipolar cycloaddition of nitrone
  • Carbonyl-ene reaction
  • Cationic cobalt complex
  • Chemical fixation of carbon dioxide
  • Chiral Lewis acid
  • Cobalt complex
  • Hetero Diels-Alder reaction
  • Kinetic resolution
  • Nitro-aldol reaction

ASJC Scopus subject areas

  • Organic Chemistry

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