Helical silica were prepared and functionalized by Mn(III)-salen complexes in order to catalyze asymmetric hetero-Diels–Alder reactions. Characterizations revealed doping of sodium lactate facilitated porosity, hydrolysis resistance and chiral configuration of silica matrix. Catalysis revealed the combination of Mn(III)-salen with helical silica had excellent chiral induction. Major product configuration was affected by temperature and solvent. Loading imidazolium ionic liquid as solvent improved both enantioselectivity and catalyst recycling.