Class II Directed Carbometalation Processes for Heterocycle Synthesis

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DESCRIPTION (provided by applicant): Synthetic organic chemistry plays a central role in the discovery and production of molecules with biological and medical significance. The long-term goal of our laboratory is to advance synthetic methods and strategies that allow for new directions in the discovery of such entities. This proposal describes the development of a suite of synthetic methods for the preparation of nitrogen-containing small molecules (acyclic and heterocyclic). As molecules of this class have been quite successful in the development of small molecule therapeutics, methods that facilitate the construction of such architectures are important for advancing biology, medicine, and public health. The central focus of this work is the development of bimolecular carbometalation reactions of substituted olefins and alkynes with azametallacyclopropenes, enabled by stepwise encapsulation of the metal center with heterobidentate organic ligands. Overall, we describe new methods for the synthesis of ene-1,5-aminoalcohols, saturated 1,5-aminoalcohols, piperidines, pyrroles, lactams and pyrroloindolines.