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Synfacts 2009(7): 0756-0756  
DOI: 10.1055/s-0029-1217282
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Silver-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition

Contributor(s): Mark Lautens, Praew Thansandote
C.-J. Wang*, Z.-Y. Xue, G. Liang, Z. Lu
Wuhan University, P. R. of China
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

Expanding on their Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides (J. Am. Chem. Soc. 2008, 130, 17250), the authors report a silver-catalyzed version which encompasses a broader scope of substrates. The present system is compatible with azomethine ylides derived from glycinates as well as α-substituted α-amino acids. The reaction also tolerates a variety of substituents on the ylide with varying electronic and steric properties.