Exo-Selective Enantioselective Nitrone Cycloaddition

doi:10.1055/s-2005-869917

Synfacts 2005(0): 0045-0045
DOI: 10.1055/s-2005-869917

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Exo-Selective Enantioselective Nitrone Cycloaddition

Contributor(s): Hisashi Yamamoto, Matthew Boxer

H. Suga*, T. Nakajima, K. Itoh, A. Kakehi
Shinshu University, Nagano, Japan
Highly Exo-Selective and Enantioselective Cycloaddition Reactions of Nitrones Catalyzed by a Chiral Binaphthyldiimine-Ni(II) Complex
Org. Lett. 2005, 7: 1431-1434

Abstract

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Key words

1,3-dipolar cycloaddition - nitrones - nickel

Significance

<P>1,3-Dipolar cycloadditions of nitrones and olefins are excellent means for the construction of isoxazolidines as well as γ-amino alcohols. This paper describes a Ni(II) catalyst that provides exceedingly high exo-selectivity accompanied by excellent enantioselectivities with catalyst loadings as low as 5 mol%.</P>

Comment

<P>Chiral amino alcohols are important building blocks in many bio-active compounds. This communication is a standout example in that perfect exo-selectivity was obtained in many cases. The use of thiazolidinethiones as key substrates in the Binim-DCOH-Ni(II) (structure not known) catalyzed reaction also has interesting implications in the catalyst structure and function. </P>

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