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Synfacts 2005(2): 0235-0235  
DOI: 10.1055/s-2005-916077
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Resolution of Azomethine Imines Using a Dipolar Cycloaddition of Alkynes

Contributor(s): Mark Lautens, Andrew Martins
A. Suárez, C. W. Downey, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

Under conditions of low catalyst loading, racemic azomethine imines can be resolved to their respective enantiomers via Cu(I)-catalyzed [3+2] dipolar cycloaddition. Selectivity factors are generally high (15-96), and the ee of products are not greatly affected by the electronic nature of the substitutents.