The chemistry of hybrid solids constructed from organic linkers and metal nodes has received much recent attention, owing to the propensity of incorporating and fine-tuning desired properties via judicious choices of their building blocks. The Lin group has explored the rational design of functional solids based on metal-organic frameworks over the past few years. In this talk, I would like to discuss our recent success in the design and synthesis of chiral porous materials based on metal-organic frameworks by connecting metal nodes with chiral bridging ligands that have orthogonal functionalities. Two complementary strategies have been successfully utilized to synthesize catalytically active chiral MOFs. In the first approach, the primary functional groups are linked by metal-connecting units to form extended networks whereas the orthogonal secondary chiral groups can then be used to generate asymmetric catalytic sites by coordinating to a secondary metal center. In the second approach, the primary functional groups are used to generate robust transition metal precatalysts which are then linked by the metal nodes to form porous extended networks via the secondary functional groups. The catalytically active chiral porous solids have been used for highly enantioselective asymmetric catalysis by both Lewis acids and group 8 metal complexes. The present complementary synthetic strategies have thus led to ideal heterogeneous asymmetric catalysts in which both the catalytic sites and the secondary environments around them are identical throughout the solid. In comparison to other immobilization approaches, the present strategy allows the synthesis of heterogeneous asymmetric catalysts with higher catalyst loading and more accessible catalytic centers.