Stereoselective Indium-Mediated Reactions for Organic Synthesis

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This project addresses the discovery and development of indium-mediated reaction chemistry through three complementary sets of studies. The breadth and scope of indium(+3) activation of allyl halides will be evaluated, encompassing intra- and intermolecular Friedel-Crafts arylations and examining other nucleophiles as well. Diastereo- and enantioselective indium-mediated allylation of hydrazones will also be explored. Finally, indium-mediated allylation of aldehydes and imines will be studied, utilizing palladium catalysis to generate the reactive indium complexes.Chiral amines and alcohols are found in a wide variety of biologically active molecules, and the discovery and development of selective and environmentally benign methods for their preparation represents an ongoing challenge. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Gregory R. Cook, of the Department of Chemistry at North Dakota State University at Fargo. Professor Cook has formulated new indium-mediated methods for the synthesis of chiral amines and alcohols and has utilized these methods for the synthesis of biologically active compounds. The utility of indium metal as a promoter of organic reactions is highly significant due to its relatively low toxicity and compatibility with environmentally benign solvents. Professor Cook's studies in indium-mediated mild cyclization chemistry set the stage for new asymmetric eco-friendly processes for organic synthesis. Students from Sierra Leone, China, India, Japan and the US are participating in this research program.