Syntheses Of Chiral Sulfobinaphtho-Crown Ethers And Their Catalytic Properties For The Three-Component Mannich Reaction In Water

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 diastereoselectivity 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.