New Methods for the Asymmetric Synthesis of Amines

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AbstractIn this project funded by the Chemical Catalysis Program of the Chemistry Division, Professor Jonathan Ellman of Yale University is developing efficient new strategies for the asymmetric synthesis of chiral amines, which are important motifs in pharmaceuticals, agrochemicals and new materials. The broader impacts of this work include the potential for the development of new and practical methods for the asymmetric synthesis of important classes of chiral amines applicable to the preparation of pharmaceuticals, agrochemical and materials. In addition, Professor Ellman regularly participates in Yale's Science, Technology and Research Scholars program by providing opportunities for underrepresented minority and women scientists to carry out research in his laboratory. Professor Ellman also participates in the Yale University Science Pathways program, which actively supports New Haven middle and high school students interested in science.The research program has two main parts. One part relies on the practical asymmetric synthesis of aminoboronic acid derivatives that are engaged through transition metal catalysis to react with a variety of different carbon electrophiles to give valuable chiral amine products. In the second research area asymmetric organocatalysis is used to couple nucleophiles with substituted nitroalkenes. Reduction of the nitro group then provides chiral branched amine products. A key step in this strategy is enantioselective nitronate protonation, which has not previously been investigated.