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Synfacts 2009(7): 0748-0748  
DOI: 10.1055/s-0029-1217274
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective [3+3] Cycloaddition of Allenoates with Aziridines

Contributor(s): Mark Lautens, David A. Candito
H. Guo, Q. Xu, O. Kwon*
University of California, Los Angeles, USA
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

The authors report a diastereo­selective formal [3+3] cycloaddition between ­allenoates and aziridines for the formation of ­tetrahydropyridines. This represents the first report of the coupling of aziridines with phosphonium enolate intermediates. It is noteworthy that the α-, β- and β′-carbon atoms of the allenoate are incorporated into the ring.