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Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts

Jeremiah P. Malerich, Koji Hagihara and Viresh H. Rawal*

*Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, Email: vrawaluchicago.edu

J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc., 2008, 130, 14416-14417.

DOI: 10.1021/ja805693p



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Abstract

A (-)-cinchonine modified squaramide, easily prepared through a two-step process from methyl squarate, was shown to be an effective catalyst, even at catalyst loadings as low as 0.1 mol%, for the conjugate addition reactions of 1,3-dicarbonyl compounds to β-nitrostyrenes. The addition products were obtained in high yields and excellent enantioselectivities.

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Key Words

Organocatalysis, Nitro Compounds, Michael Addition


ID: J48-Y2008-3240