Research Projects

Transition metal-catalyzed asymmetric synthesis is crucial for the construction of bioactive molecules, pharmaceuticals, and natural products. Chiral ligands play a significant role in causing chirality, with 1,10-phenanthroline ligands being an effective backbone. However, their availability is limited due to the lack of a sp3 center for guiding chirality. Common chiral phenanthroline ligands face modification issues and conformational fixation issues due to the free C-C bond rotation between phenanthroline and chiral moiety. To address these issues, N,N,N-tridentate chiral phenanthrolines with axially chiral heterobiaryls are proposed. Different classes of benzophenanthrolines attached with axially chiral heterobiaryls are also designed, with cinchonidine-based benzophenanthroline attached with axially chiral heterobiaryl being designed. Diazo compounds are considered useful synthons for organic transformations, particularly in stereoselective synthesis. The developed axially chiral heterobiaryl ligands can be used with suitable transition metals to bring the appropriate chiral environment during stereoselective transformations using diazo compounds as starting materials. The asymmetric synthesis of 3,3 disubstituted oxindole derivatives via domino Heck/arylation using quinone diazide as coupling partner is proposed. Stereoselective cycloaddition strategies using enoldiazoacetate and 2-pyridone are also proposed. Stereoselective oxyalkynylations are planned using quinone diazide and hypervalent iodine-based reagents. Desymmetrization of para-quinamine with diazo partner is also planned using the proposed bifunctional chiral ligand.