Ten 6,6'-disulfobinaphtho-crown ethers were synthesized via sulfonization of the corresponding crown ethers. Chiral sulfobinaphtho-crown ethers were used to catalyze the 3-component Mannich reaction of analine, benzaldehyde and cyclohexanone in aqueous media and show excellent yield and diastereoselec-tivity up to de 98%. Investigation into the reactions of analine/substituted analine, benzaldehyde and hypnone demonstrates that the molecular structures of the catalysts and the substrate compounds, as well as the reaction temperature and time can influence the catalytic results.

Key words: sulfonization, chiral catalyst, Mannich reaction, synthesis, crown ether, 1,1'-bi-2-naphthol (BINOL)