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Synfacts 2009(4): 0400-0400  
DOI: 10.1055/s-0028-1087900
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

1,3-Dipolar Cycloaddition of Azomethine Ylides with α,β-Unsaturated Ketones

Contributor(s): Mark Lautens, Jacki Kitching
J. Hernández-Toribio, R. G. Arrayás, B. Martín-Matute, J. C. Carretero*
Universidad Autónoma de Madrid, Spain
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

The copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with α,β-unsaturated ketones is described. Reaction with 2-cyclopentenone afforded products with endo selectivity, whereas reaction with the trans-acyclic enones gave high exo selectivity. A stereochemical model that depicts the most stable geometry (based on computational studies) in the coordination of the metal atom with the ligand and azomethine species is provided to rationalize the observed selectivities.