Chinese Journal of Catalysis ›› 2008, Vol. 29 ›› Issue (4): 351-355.

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Immobilization of L-Proline on SBA-15 and Its Application in Asymmetric Mannich Reaction

SUN Caixia, LI Haigang, WU Haihong*, LIU Yueming, WU Peng   

  1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China
  • Received:2008-04-25 Online:2008-04-25 Published:2012-03-22

Abstract: The novel Pro/SBA-15 catalyst was prepared using SBA-15 zeolite as the support to immobilize L-proline (Pro) derivatives, which was synthesized from 4-hydroxy-L-proline. The Pro/SBA-15 catalyst was characterized byX-raydiffraction, N2 adsorption-desorption, scanning electron microscopy, and infrared spectroscopy. The catalytic performance of the catalyst was measured for asymmetric Mannich reaction. The results indicated that the mesoporous structure of SBA-15 was not affected by immobilization, however, the pore diameter, pore volume, and BET surface area were decreased. The Pro/SBA-15 catalyst had higher catalytic activity and enantioselectivity. Using 4-nitrobenzaldehyde as the reactant, the Mannich reaction product was obtained with high yield (80%) and moderate enantioselectivity (ee=60%). The supported catalyst could be easily separated from the reaction system and reused at least four times without loss of activity and enantioselectivity.

Key words: 4-hydroxy-L-proline, SBA-15 zeolite, supported catalyst, asymmetric Mannich reaction, 4-nitrobenzaldehyde