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The prevalence of nitrogen heterocycles in medicinally important compounds has, for years, inspired synthetic chemists for developing strategies to form new heterocyclic scaffolds and methods that streamline the syntheses of complex heterocycles. Giving into the cause, this dissertation primarily focuses on development of transition-metal catalyzed hydroacylation of alkenes as a platform for enantioselective synthesis of multiple classes of polycyclic nitrogen heterocycles. Development of catalytic, enantioselective intramolecular hydroacylation of Nvinylindole-2-carboxaldehydes that occur in the presence of a readily accessible rhodium catalyst and form chiral, non-racemic 2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ones in high yields and enantioselectivities has been described. The dihydropyrroloindolone products can be readily transformed to dihydropyrroloindoles that are core structures present in a variety of natural products and biologically relevant compounds. This methodology could be extended to hydroacylations of N-allylindoleand N-allylpyrrole-2-carboxaldehydes in construction of six-membered rings that generated 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities. In contrast to many alkene hydroacylations that form six-membered rings, these endo-selective annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. Our protocol for rhodium-catalyzed hydroacylation of N-vinylindole-2carboxaldehyde could be leveraged for installation of stereochemical triad in 2,3-dihydro1H-pyrrolo[1,2-a]-indole core of putative structure of yuremamine. The enantioselective model synthesis was achieved in 39% overall yield and 96% ee over 5 steps. An

Transition Metal-Catalyzed Alkene Hydroacylation as a Platform for Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles