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Synfacts 2007(1): 0073-0073  
DOI: 10.1055/s-2006-955732
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed Asymmetric Synthesis of α,β-Unsaturated δ-Lactones

Contributor(s): Mark Lautens, Yann Béthuel
B. Bazán-Tejeda, G. Bluet, G. Broustal, J.-M. Campagne*
Institut de Chimie des Substances Naturelles, Gif-sur-Ivette, France
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

Over the last decade, the vinylogous Mukaiyama reaction has been widely used as an efficient synthetic tool in total synthesis. Recently, Evans and co-workers (J. Am. Chem. Soc. 2002, 124, 5654-5655) and Denmark and coworkers (J. Am. Chem. Soc. 2003, 125, 7800-7801) described excellent regio-, diastereo- and enantioselectivities in this reaction. In the present paper, the authors report their own study on the catalytic and asymmetric vinylogous Mukaiyama reaction towards the synthesis of α,β-unsaturated δ-lactones using Carreira’s catalyst (J. Krueger, E. M. Carreira J. Am. Chem. Soc. 1998, 120, 837-838).