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Synfacts 2009(4): 0413-0413  
DOI: 10.1055/s-0028-1087897
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Gold-Catalyzed Enyne Cyclization

Contributor(s): Mark Lautens, Jane Panteleev
C.-M. Chao, M. R. Vitale, P. Y. Toullec, J.-P. Genêt, V. Michelet*
Ecole Nationale Supérieure de Chimie de Paris, France
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

The authors describe a tandem cycloisomerization of 1,6-enynes using a gold catalyst and aromatic nucleophiles. Although this class of reactions is well characterized (see Review below), enantioselective variants are much less common. A moderate scope is demonstrated achieving high yields and enantioselectivities.

Review: N. Bongers, N. Krause Angew. Chem. Int. Ed. 2008, 47, 2178-2181.