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Synfacts 2005(0): 0045-0045  
DOI: 10.1055/s-2005-869917
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

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  
CrossrefPubMed
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

1,3-dipolar cycloaddition - nitrones - nickel

Significance

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%.

Comment

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.

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