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Synfacts 2008(4): 0418-0418  
DOI: 10.1055/s-2008-1042829
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

A New Class of Hydrogen-Bonding Catalysts: N-Sulfinyl Ureas

Contributor(s): Benjamin List, Daniela Kampen
M. T. Robak, M. Trincado, J. A. Ellman*
University of California, Berkeley, USA
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Chiral N-sulfinyl ureas have been developed as catalysts for an asymmetric aza-Henry reaction. Addition of nitroalkanes 3 to both aromatic and aliphatic N-Boc imines 2 in the presence of organocatalyst 1 (10 mol%) and i-Pr2NEt (50 mol%) gives protected nitroamines 4 in high yields, syn-diastereoselectivities, and enantio­selectivities. The authors present examples of enantioselective hydrogen-bonding-catalyzed additions to aliphatic N-Boc imines.