Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α,β-Unsaturated Aldehydes Catalyzed by Cationic 3-Oxobutylideneaminatocobalt(III) Complexes
Satoko KezukaNatsuki OhtsukiTsuyoshi MitaYouichi KogamiTomoko AshizawaTaketo IkenoTohru Yamada
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2003 Volume 76 Issue 11 Pages 2197-2207


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(II) 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.

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© 2003 The Chemical Society of Japan
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