RUI: Catalytic Methods for the Enantioselective Synthesis of Enolizable Alpha-Amino and Alpha-Azido Aldehydes and Novel Applications Thereof

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This award from the Chemical Synthesis program supports the research and development of new methods for constructing alpha-amino aldehydes and related structures in the laboratory of Professor Thomas Coombs at the University of North Carolina Wilmington (UNCW). The nitrogen sources used in this work allow easy manipulation of the nitrogen protecting group following their union with aldehydes. The ability to remove this protecting group using mild reaction conditions is expected to permit a broader range of functionalized aldehydes to serve as starting materials in streamlined syntheses of nitrogen-containing small molecules. The alpha-amino aldehydes generated via these methods can be transformed into a range of nitrogen-containing compounds with potential applications in medicinal chemistry and chemical biology. The proposed chemistry uses organocatalysts and water in the key steps, contributing to the development of this line of catalytic bond construction. The University of North Carolina Wilmington (UNCW) has a strong tradition of training students in STEM fields. This award will allow Professor Coombs to extend hands-on research opportunities to both undergraduate and M.S.-level students interested in conducting original research in preparation for careers in chemical science. The projects funded in this proposal will be used to teach students how to approach research questions from a molecular perspective and to troubleshoot challenges encountered in the laboratory.The proposed research is aimed at developing new methods for the enantioselective organocatalytic synthesis of enolizable alpha-amino aldehydes bearing sulfonamide protecting groups. These protecting groups may be removed under non-reductive conditions, permitting the incorporation of reducible functional groups in the starting aldehydes. Extending these methods to use tryptamines as reaction substrates for the synthesis of 3-amino-pyrroloindolines via a similar mechanism will also be investigated, as will the development of an enantioselective route to enolizable alpha-azido aldehydes for use in tandem reactions generating nitrogen heterocycles. The proposed research seeks to develop new enantioselective amination methods for streamlining organic synthesis.