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Synfacts 2008(5): 0506-0506  
DOI: 10.1055/s-2008-1072670
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Oxaziridines as Nitrone Precursors for [2+3] Cycloadditions

Contributor(s): Mark Lautens, Frédéric Ménard
K. M. Partridge, M. E. Anzovino, T. P. Yoon*
University of Wisconsin-Madison, USA
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Publikationsdatum:
23. April 2008 (online)

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Significance

The first cycloaddition of N-sulfonyl nitrones with alkenes is reported to occur under Lewis acid catalysis from simple oxaziridines, extensively studied by Davis. The products obtained are cis-disubstituted 1,2-isoxazolidines 3. The method is complementary to a previous report from the same group which provided regio­isomeric 1,3-oxazolidines under Cu(II) catalysis (J. Am. Chem. Soc. 2007, 129, 1866; Synfacts 2007, 498). The reaction is regioselective and proceeds with high diastereoselectivity.