Organic Chemistry Portal



Pyridinium 1,1'-Binaphthyl-2,2'-disulfonates as Highly Effective Chiral Brønsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction

Manabu Hatano, Toshikatsu Maki, Katsuhiko Moriyama, Manabu Arinobe and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan, Email:

M. Hatano, T. Maki, K. Moriyama, M. Arinobe, K. Ishihara, J. Am. Chem. Soc., 2008, 130, 16858-16860.

DOI: 10.1021/ja806875c

see article for more reactions


An efficient enantioselective catalysis in the Mannich-type reactions of diketones and ketoester equivalents with aldimines was developed using a chiral combined salt of chiral 1,1′-binaphthyl-2,2′-disulfonic acid with 2,6-diarylpyridine, which acted as convenient chiral tailor-made Brønsted acid-base organocatalysts in situ.

see article for more examples

Key Words

Mannich Reaction, Organocatalysis, β-amino ketones, active methylenes

ID: J48-Y2008-3800