Research Projects

Development of sustainable, efficient, and selective organic synthesis is one of the fundamental challenges in organic chemistry, which will immensely benefit the chemical and pharmaceutical industries and eventually to the environment and humankind. In particular, selective synthesis of specific enantiomer has been an everlasting problem for an organic chemistry and drug discovery, since the enantiomers may differ in their activity with target that could exhibit either desired or detrimental effect. In this context, transition metal catalyzed enantio- and diastereoselective transformations have emerged as the key technology to address the current growing demand for chiral molecules in various fields. These transformations are highly controlled by the presence of chiral ligands, which are key to any asymmetric transformation. Although the typical phosphine and nitrogen based chiral ligands have seen tremendous growth and recently studies have demonstrated the efficiency of chiral cyclopentadiene ligands, other prevalent ligand such as arene based chiral ligands are rather limited. Hence, the present proposal aims to design and develop new classes of chiral C2-symmetric arenes from readily available chiral building blocks, such as BINOL and SPINOL. The synthesized chiral ligands will be employed in the construction of various ruthenium(II) complexes. Utilizing the developed ruthenium(II) catalysts, a new class of asymmetric alkylation involving C-H bond functionalization with alkyl halides at ortho and meta-position, asymmetric alkylation with alkenes, desymmetrization, asymmetric annulation for the synthesis of axially chiral and spiro compounds will be executed. The successful development of these strategies would result; 1) will introduce new classes of chiral arene ligands and give a new approach in the ruthenium catalyzed asymmetric reaction, 2) new, rapid and clean synthesis of various potential chiral building blocks, heterocyclic and polycyclic scaffold, and 3) will deliver a new class of asymmetric transformation. Furthermore, application of the developed methodologies will be demonstrated through the enantioselective synthesis of lycorane-type and lycoris alkaloids.