Application of Sulfinamides in Synthesis and Catalysis

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Jonathan Ellman of the Department of Chemistry at Yale University will develop methods for the asymmetric synthesis of amine-containing compounds using tert-butanesulfinamide. Powerful new methods for the efficient asymmetric synthesis of alpha-branched amines will be developed through the highly functional group compatible addition of organozinc and organoboron reagents to N-tert-butanesulfinyl imines. New sulfinamide-based organocatalysts will also be developed as a general new class of catalysts for the highly efficient synthesis of amine-containing compounds applicable to the production of bioactive drugs and agrochemicals.The proposed work has broad impact because more than 80% of all drugs and drug candidates contain amine functionality, and many of these amine-containing compounds are also chiral. tert-Butanesulfinamide chemistry, developed in Professor Ellman's lab largely with NSF support, is one of the most extensively used methods for the preparation of amine containing compounds in the pharmaceutical, biotechnology and agrochemical industries as well as in academic chemical biology research. The research proposed here could further enhance the utility of this chemistry and consequently accelerate scientific advances, including the discovery of new drugs to treat unmet medical conditions. Moreover, the proposed work will involve training undergraduate and graduate students, including those from groups currently underrepresented in the sciences.