Syntheses Of Chiral Sulfobinaphtho-Crown Ethers And Their Catalytic Properties For The Three-Component Mannich Reaction In Water
CHINESE JOURNAL OF ORGANIC CHEMISTRY(2007)
Abstract
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.
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Key words
1,1 '-bi-2-naphthol (BINOL), crown ether, sulfonization, chiral catalyst, Mannich reaction, synthesis
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