The concept of bifunctional asymmetric catalysis is very powerful for designing new enantioselective catalysts. We describe our investigation starting with the development of a BINOL-derived Lewis acid-Lewis base bifunctional asymmetric catalyst for cyanosilylation of aldehydes. The initial establishment of the concept was followed by the development of new sugar-derived catalysts that promote general catalytic enantioselective cyanosilylation of ketones. We also describe the catalytic enantioselective Reissert reaction of pyridine derivatives and Strecker reaction of ketoimines as recent advances in this field. 1 Introduction 2 General Concept of Lewis Acid-Lewis Base Bifunctional Asymmetric Catalysis 3 Catalytic Enantioselective Cyanosilylation of Aldehydes and Aldimines 4 Catalytic Enantioselective Reissert Reaction of Quinolines and Isoquinolines 5 Catalytic Enantioselective Reissert Reaction of Pyridine Derivatives 6 Tetrasubstituted Carbon Construction as a Challenge in Asymmetric Catalysis 7 Catalytic Enantioselective Cyanosilylation of Ketones 8 Catalytic Enantioselective Strecker Reaction of Ketoimines 9 Summary