Research Projects

The stereoselective synthesis of chiral polyaryl compounds—particularly those featuring medium-sized bridged frameworks—remains a significant challenge in modern organic synthesis. The difficulties arise not only from the need to control multiple elements of chirality but also from the inherent ring strain and high energy barriers associated with constructing medium-sized rings. As a result of these challenges, the stereoselective construction of eight- and nine-membered bridged aryl systems remains underexplored and poorly documented, whereas significant emphasis has traditionally been laid on the synthesis of five- and six-membered, and to a lesser extent seven-membered, carbo- and heterocyclic rings. This research project aims to address these synthetic limitations by developing new catalytic asymmetric methodologies, primarily utilizing small organic molecules (organocatalysts), to access structurally complex and stereochemically pure bridged polyaryls. The targeted compounds include biaryl and triaryl systems featuring eight- or nine-membered bridges, which are of particular interest due to their multiple chirality elements—central chirality, atropisomerism, and inherent chirality. These rigid, three-dimensional architectures impart excellent configurational stability and are valuable scaffolds in bioactive molecules, natural product analogues, chiral catalysts, and systems for molecular recognition. Despite their promising potential, synthetic methods for constructing such inherently chiral and atropisomeric architectures—especially those involving medium-sized rings—are limited. Leveraging the catalytic potential of organocatalysts, this project will explore the following complementary strategies to access these medium-sized bridged biaryl and triaryl systems in enantio- and diastereoselective fashion: • Direct intermolecular nucleophilic addition to medium-sized biaryl and triaryl electrophiles. • Intramolecular cyclization strategies to construct medium-sized rings. • Domino or cascade reactions enabling the generation of multiple chirality elements in a single operation. • Merger of organocatalysis with photoredox catalysis or electrochemical redox process. • Dynamic kinetic resolution (DKR) and kinetic resolution (KR) approaches for the enantioenrichment of racemic precursors. • Desymmetrization of a planar medium-sized biaryl and triaryl acceptors. By designing highly stereoselective organocatalytic methodologies, this work aims to significantly expand the synthetic toolbox for constructing architecturally sophisticated, functionally rich medium-sized bridged bi- and tri-aryl systems.