Cyclohexane-1,2-diamines as Catalysts

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.