The design, synthesis and use of chiral ligands in various organic reactions: applications toward the asymmetric synthesis of natural products

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The goal of this proposal is to design, prepare and use new chiral ligands and chiral Lewis acids within certain key steps towards the asymmetric synthesis of natural products exhibiting interesting biological activity (anticancer properties, etc.). These new chiral entities are used in conjunction with metals (Pd, Rh, Ru, etc.) and Lewis acids (Al) in reactions that preferentially form one enantiomer in excess over the other. Other asymmetric reactions being studied include intra- and inter-molecular Diels Alder reactions, metal-catalyzed anion capture reactions and rhodium-catalyzed hydrogenations. The mechanism(s) of these reactions are studied using isotopes, a variety of NMR techniques and/or theoretical calculations (semi-empirical and DFT). We also execute some of these asymmetric reactions under high pressures and/or using microwaves.