Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α,β-Unsaturated Aldehydes Catalyzed by Cationic 3-Oxobutylideneaminatocobalt(III) Complexes

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

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52 Citations (Scopus)

Abstract

The enantioselective 1,3-dipolar cycloaddition reaction of nitrones with α,β-unsaturated aldehydes was realized using 3-oxobutylideneaminatocobalt complex catalysts. Varieties of the cobalt(III) and cobalt(III) complexes were screened and the cationic cobalt(III) complex with hexafluoroantimonate was found to be the most effective for the catalytic enantioselective 1,3-dipolar cycloaddition reaction. In the presence of the cobalt(III) hexafluoroantimonate complex, the enantioselective 1,3-dipolar cycloaddition reaction of various nitrones with α,β-unsaturated aldehydes afforded the corresponding isoxazolidines in high yields and with high enantioselectivities. The absolute configuration of the optically active products was determined by X-ray analysis. Reasonable explanations for the enantioselection in the present 1,3-dipolar cycloaddition reaction catalyzed by the 3-oxobutylideneaminatocobalt complex were proposed.

Original languageEnglish
Pages (from-to)2197-2207
Number of pages11
JournalBulletin of the Chemical Society of Japan
Volume76
Issue number11
DOIs
Publication statusPublished - 2003 Nov 1

ASJC Scopus subject areas

  • Chemistry(all)

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