Enantiopure chiral molecules are critically important in many areas of industrial and medicinal chemistry, including drug therapies. In particular, within the pharmaceutical industry, the chirality of a drug molecule must be carefully considered as its “non-active” enantiomer can have a dramatically different impact in the body including seriously grave ones. Preparation of enantiopure molecules is thus necessary to avoid such adverse impacts, and other issues, where possible. Numerous methods exist to prepare enantiopure molecules with metal-mediated enantioselective catalysis being particularly successful. The continued development of chiral ligands for metal-mediated enantioselective catalysis is needed develop efficient systems to catalyze a wide range of reactions for substrates with various functional groups. Herein we report on the continuing studies of our group’s designed C2 symmetric, mer-coordinating, bis(4,5-dihydrooxazol-2-ylimino)isoindoline-based pincer ligands for use in metal-mediated enantioselective catalysis reactions. Attempted optimization of the ligand synthesis through the use of calcium or magnesium-based Lewis acid catalysts in a one-pot reaction under microwave conditions is reported. NMR and x-ray crystallographic (in some cases) characterizations of the isolated products stemming from these reactions, including metal-ligand complexes, are included. Additionally, preliminary enantioselective catalysis studies using our ligand system in palladium-catalyzed enantioselective hydrophosphination of enones are presented.

Chiral mer-coordinating bis(4,5-dihydrooxazol-2-ylimino)isoindoline-based pincer ligands: Attempted synthesis optimization, characterization, and preliminary enantioselective catalysis studies

254th National Meeting (2017)

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