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Synfacts 2010(2): 0228-0228  
DOI: 10.1055/s-0029-1219127
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Phosphite Addition to Nitroalkenes Using Squaramide Catalysis

Contributor(s): Benjamin List, Olga Lifchits
Y. Zhu, J. P. Malerich, V. H. Rawal*
The University of Chicago, USA
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

Having recently introduced the squaramide motif in hydrogen-bonding catalysis (J. Am. Chem. Soc. 2008, 130, 14416), Rawal and colleagues now demonstrate its high efficiency in the Michael addition of diphenyl phosphite to nitroalkenes. Excellent enantiomeric induction and yields were observed for a range of nitroalkene substrates. Aliphatic and aromatic nitroalkenes were found to be equally suitable substrates.