Water-treated SBA-15 Supported Quinine for Asymmetric Michael Addition Reaction

• 1、College of Environmental Science and Engineering, Nankai University, Tianjin 300071
• 2、Institute of New Catalytic Materials Science, College of Chemistry, Nankai University, Tianjin 300071

Abstract：The heterogenization of cinchona alkaloids has attracted more and more attention in the recent years. Quinine immobilized on conventional SBA-15 provides low activity in the asymmetric Michael addition of malononitrile to chalcones. In this paper, SBA-15 was treated with water to increace the population and uniform dispersion of surface hydroxyl groups, and then used to immobilize quinine, to build an effective heterogeneous chiral organic catalyst for the asymmetric Michael addition of malononitrile to chalcones. The results of XRD, FT-IR, nitrogen sorption, TG, SEM and TEM showed that quinine was successfully immobilized on water-treated SBA-15, and that the long-range mesoporous ordering of parent supports was maintained after the immobilization. And the loadings of mercaptopropyl and quinine increased after SBA-15 was treated with water. The heterogeneous catalysts exhibited higher activity and enantioselectivity than the catalyst supported on conventional SBA-15. In particular, when 4-methoxy chalcone was test, an excellent ee value up to 78% was obtained, which was much higher than that of conventional catalyst and even higher than the corresponding homogeneous catalyst.

Keywords： Heterogeneous organic catalysis Water-treatment SBA-15 Quinine Asymmetric Michael addition