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Synfacts 2011(6): 0640-0640  
DOI: 10.1055/s-0030-1260400
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Au(I)-Catalyzed Asymmetric Cycloadditions and Mannich Reactions of Azlactones

Contributor(s): Mark Lautens, Hasnain A. Malik
A. D. Melhado, G. W. Amarante, Z. J. Wang, M. Luparia, F. D. Toste*
University of California, Berkeley, USA
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

The authors report gold(I)-catalyzed asymmetric 1,3-dipolar cycloadditions and Mannich reactions of azlactones. Studies are carried out to elucidate the nuances of the mechanism of stereoinduction in these reactions. Furthermore, tandem MS and kinetic studies are undertaken in order to deduce possible mechanistic pathways. The authors propose a mechanism for both reaction pathways from common ­intermediates.