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Synfacts 2011(6): 0649-0649  
DOI: 10.1055/s-0030-1260401
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantio- and Diastereoselective Aldol Reaction of Thioamides

Contributor(s): Mark Lautens, Hasnain A. Malik
M. Iwata, R. Yazaki, I-H. Chen, D. Sureshkumar, N. Kumagai*, M. Shibasaki*
Institute of Microbial Chemistry, Tokyo and The University of Tokyo, Japan
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

The authors disclose a copper(I)-catalyzed enantio- and diastereoselective aldol ­reaction of thioamides and aldehydes. Although there has been considerable interest from the synthetic community in the field of direct catalytic asymmetric aldol methodology, to date there have been a limited number of publications utilizing aldol donors in the carboxylic acid oxidation state. The authors demonstrate the synthetic utility of their products by converting the thioamide moiety into an aldehyde, ketone, 1,3-dicarbonyl, amide or a primary amine functionality.