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
see article for more reactions
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.
see article for more examples
Key Words
Organocatalysis, Nitro Compounds, Michael Addition
ID: J48-Y2008-3240