Silica-based helical rod supporting guanosine compounds catalyzed asymmetric hetero-Diels–Alder reaction

• Silica-based helical rods were prepared under chiral sodium lactate in sol–gel.
• Helical rod had a hierarchical structure including morphology and internal channel.
• Configuration of internal channel of helical supports was all right-handed.
• Guanosine derivatives show catalytic activity in hetero-Diels–Alder reaction.
• Helical rod supporting guanosine catalyzed chiral hetero-Diels–Alder reaction.

A series of silica-based helical rods were prepared and functionalized for immobilization of guanosine compounds in catalytic asymmetric hetero-Diels–Alder reaction. Nitrogen physisorption, electron microscopy and amino acid adsorption revealed that helical rod has a hierarchical structure including morphology and internal channels, and doping of sodium lactate facilitates porosity and internal chirality of synthetic rods. Catalysis revealed that guanosine derivatives were catalytically active, combination of guanosine with L-sodium lactate-doped rod was more enantioselective than that with zero- or D-sodium lactate-doped samples, and recycling of supported Schiff-base-guanosine was stable during six cycles.