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Synfacts 2011(4): 0409-0409  
DOI: 10.1055/s-0030-1259657
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Vinylogous and Bisvinylogous Aldol Reactions

Contributor(s): Hisashi Yamamoto, Patrick Brady
L. Ratjen, P. García-García, F. Lay, M. E. Beck, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr and Bayer CropScience AG, Monheim am Rhein, Germany
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

The authors describe a catalytic system for asymmetric vinylogous aldol addition and an unprecedented asymmetric bisvinylogous aldol addition, furnishing ε-siloxy α,β,δ,γ-unsaturated esters in high yield and selectivity. The system employs a pre-Lewis acidic disulfonimide ­catalyst that has previously been applied to the asymmetric Mukaiyama aldol reaction.