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Synfacts 2009(5): 0556-0556  
DOI: 10.1055/s-0029-1216575
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclohexane-1,2-diamines as Catalysts

Contributor(s): Benjamin List, Frank Lay
R. Rasappan, O. Reiser*
Universität Regensburg, Germany
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

The authors report monosulfonated cyclohexane-1,2-diamines (1) as catalysts for the conjugate addition of aromatic ketones to β-nitro-styrenes. Moderate to high yields and excellent enantioselectivities are achieved. Furthermore, a reaction pathway for catalyst deactivation resulting in the irreversible formation of pyrroles has been recognized.

Reviews: S. Sulzer-Mossé, A. Alexakis Chem. Commun. 2007, 3123; S. B. Tsogoeva Eur. J. Org. Chem. 2007, 1701; S. Mukherjee, J. W. Yang, S. Hoffmann, B. List Chem. Rev. 2007, 107, 5471.