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Synfacts 2010(11): 1266-1266  
DOI: 10.1055/s-0030-1258808
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Vinylogous Aldol Reaction Cata-lyzed by a Combined Acid Titanium Complex

Contributor(s): Hisashi Yamamoto, Patrick Brady
G. Wang, J. Zhao, Y. Zhou, B. Wang, J. Qu*
Dalian University of Technology, P. R. of China
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The authors describe a novel titanium catalyst based on the BINOL scaffold for asymmetric vinylogous aldol addition. The reaction takes place at ambient temperatures and gives high yields and ee values for aromatic and α,β-unsaturated aldehydes. Importantly, the γ-­aldol addition product is obtained exclusively without observation of the hetero-Diels-Alder ­adduct.

Review: S. E. Denmark, J. R. Heemstra, G. L. Beutner Angew. Chem. Int. Ed. 2005, 44, 4682-4698.