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Synfacts 2011(5): 0514-0514  
DOI: 10.1055/s-0030-1259875
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Nitrone Cycloadditions with 2-Alkenoyl Pyridine N-Oxides

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
S. Barroso, G. Blay*, M. C. Muñoz, J. R. Pedro*
Universitat de València and Universidad Politécnica de Valencia, Spain
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

Isoxazolidines are valuable precursors for a number of biologically important substances; among the developed procedures available to access these compounds via copper-catalyzed 1,3-dipolar cycloadditions, only a limited number of dipolarophiles has been tested. In this paper, the authors expand the scope of the electron-deficient alkene substrates by reporting a copper(II)-BOX mediated 1,3-dipolar cycloaddition of nitrones to 2-alkenoyl pyridine N-oxides, which proceeds endo-selectively with good to excellent yields, enantio- and diastereoselectivities.