Synthesis and Applications of Asymmetric Catalysis Using Chiral Ligands Containing Quinoline Motifs

Abstract

AbstractIn the past decade, asymmetric synthesis of chiral ligands containing quinoline motifs, a family of natural products displaying a broad range of structural diversity and their metal complexes, have become the most significant methodology for the generation of enantiomerically pure compounds of biological and pharmaceutical interest. This review provides comprehensive insight on the plethora of nitrogen-based chiral ligands containing quinoline motifs and organocatalysts used in asymmetric synthesis. However, it is confined to the synthesis of quinoline-based chiral ligands and metal complexes, and their applications in asymmetric synthesis as homogeneous and heterogeneous catalysts.1 Introduction2 Synthesis of Chiral Ligands Containing Quinoline Motifs2.1 Synthesis of Schiff Base Type Chiral Ligands2.2 Synthesis of Oxazolinyl-Type Chiral Ligands2.3 Synthesis of Chiral N,N-Type Ligands2.4 Synthesis of Amine-Based Chiral Ligands2.5 Synthesis of P,N-Type Chiral Ligands2.6 Synthesis of Chiral N-Oxide and Nitrogen Ligands3 Homogeneous Catalytic Asymmetric Reactions3.1 Asymmetric Carbon–Carbon Bond Formation Reactions3.2 Asymmetric Allylic Reactions3.3 Asymmetric Cycloadditions3.4 Asymmetric Carbene Insertions3.5 Asymmetric Pinacol Couplings3.6 Asymmetric Pudovik Reactions3.7 Asymmetric Strecker Reactions4 Heterogeneous Catalytic Asymmetric Reactions4.1 Asymmetric Cyclopropanation of Olefins4.2 Asymmetric Heck Reactions4.3 Asymmetric Hydrogenations4.4 Asymmetric Hydroformylation of Styrene4.5 Asymmetric Dialkoxylation of 2-Propenylphenols4.6 Asymmetric Cascade Cyclizations4.7 Asymmetric Allylic Alkylations4.8 Asymmetric Alkylation of β-Keto Esters4.9 Asymmetric C–H Bond Arylation Reactions4.10 Intramolecular Aerobic Oxidative Amination of Alkenes4.11 Asymmetric Oxidative Hydroboration of Alkenes5 Conclusions