Asymmetric Catalysis in Confined Space Provided by l-Proline Functionalized Mesoporous Silica with Plugs in the Pore

Abstract

Mesoporous silica having l-proline functionality and plugged pore structure was synthesized by direct microwave synthesis under acidic condition using Pluronic P123 as template and sodium metasilicate nonahydrate as silica source. The direct synthesis resulted in the prismatic or disk types with short channels and plugs in the pore structure. Due to the presence of plugs, dual mesoporosities with 7 and 3 nm pore diameter were generated leading to an existence of cavitation. Tri-functionality of this materials i.e. chiral organofunctional group, plugs, and short channel, would be useful for the asymmetric diethyl malonate addition reaction and asymmetric epoxidation reaction of α,β-unsaturated aldehydes. We proved that the formation of plugs in the mesoporous silica governs the formation of dual mesoporosities providing an enhancement of enantiomeric excess in the asymmetric catalysis. This finding might open an important application of the amino-acid organo multifunctionalized mesoporous silica for asymmetric reactions.