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Catalysis Letters, Vol.142, No.11, 1405-1410, 2012
Carboxymethylcellulose Supported Cinchonine as a Recyclable Catalyst for Asymmetric Michael Reaction
A novel cinchonine catalyst supported by carboxymethylcellulose (CMC) has been prepared with a simple approach. As-prepared CMC-supported cinchonine catalyst was used to catalyze the asymmetric Michael addition of 1,3-dicarbonyl compounds to N-benzylmaleimide at a very low loading (3 mol%). It has been found that desired adducts containing adjacent quaternary and tertiary stereocenters can be obtained in high efficiency (yield 80 %) and stereoselectivity (dr 75:25, ee 78 %). Moreover, as-prepared catalyst possesses good recyclability (at least 4 times).
Keywords:Carboxymethylcellulose (CMC);Cinchona alkaloids;Cinchonine;Organocatalyst;Asymmetric Michael reaction