Enantioselective 1,3-dipolar cycloaddition reactions between nitrones and α-substituted α,β-unsaturated aldehydes catalyzed by chiral cationic cobalt(III) complexes

Natsuki Ohtsuki, Satoko Kezuka, Youichi Kogami, Tsuyoshi Mita, Tomoko Ashizawa, Taketo Ikeno, Tohru Yamada

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39 Citations (Scopus)

Abstract

The optically active β-ketoiminato cationic cobalt(III) complexes catalyzed the 1,3-dipolar cycloaddition reaction of nitrones with α,β-unsaturated aldehydes. In the reaction of nitrones derived from 2-halobenzaldehyde, excellent endo-selectivities and high enantioselectivities were observed. The α-substituted α,β-unsaturated aldehyde, such as 2-benzylpropenal, afforded the corresponding isoxazolidine in high stereoselectivity.

Original languageEnglish
Pages (from-to)1462-1466
Number of pages5
JournalSynthesis
Issue number9
Publication statusPublished - 2003 Jul 22

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Keywords

  • Aldehyde
  • Asymmetric catalysis
  • Complexes
  • Cycloadditions
  • Nitrones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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