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Synfacts 2009(1): 0094-0094  
DOI: 10.1055/s-0028-1087420
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Squaramide Organocatalysis

Contributor(s): Benjamin List, Ilija Èorić
J. P. Malerich, K. Hagihara, V. H. Rawal*
The University of Chicago, USA
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

Squaramides were identified as ­efficient catalysts for conjugate addition of 1,3-dicarbonyl compounds to β-nitrostyrenes. Readily accessible cinchonine-substituted derivative 1 is a highly active catalyst, affording products in high yields and enantioselectivities. Additionally, high diastereoselectivity was observed with configurationally stable products (R² ∂ H).