New Lewis Bases for Enantioselective Catalysis

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The discovery and tailoring of new useful organic molecules for applications such as medicine and materials science is highly driven by meaningful developments in chemical methodology, and some of the most impactful advances have invoked catalysis to increase efficiency and specificity. N-heterocyclic carbenes (NHCs) have continuously occupied a prominent space in catalytic methodology due to their unique steric features, electronic properties, and versatility as both metal ligands and organocatalysts. This thesis describes our efforts to invoke unusual molecular topology in extending the value of this ligand class in enantioselective catalysis. The first chapter details our initial attempts to incorporate metallocenes as effective control units in NHC-mediated asymmetric catalysis. The unique product of these efforts is employed in chapter two for the asymmetric synthesis of the privileged, but challenging α-aminoboronate motif. Lastly, chapter three briefly describes our initial foray into the development of exotic NHC precursors which incorporate a metal atom at the “wingtip N” position.

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  • 02/15/2019
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