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

doi:10.1055/s-2003-40194

SPECIALTOPIC

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*
Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Fax: +81(45)5661716; e-Mail: yamada@chem.keio.ac.jp;

Abstract

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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.

Key words

aldehyde - asymmetric catalysis - complexes - cycloadditions - nitrones

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References

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