White, Nicholas Andrew, authorRovis, Tomislav, advisorKennan, Alan J., committee memberChen, Eugene Y.-X., committee memberWilliams, Robert M., committee memberKipper, Matt J., committee member2016-01-112016-01-112015http://hdl.handle.net/10217/170358A series of δ-nitroesters were synthesized through the N-heterocyclic carbene catalyzed coupling of enals and nitroalkenes. The asymmetric coupling of these substrates via the homoenolate pathway afford δ-nitroesters in good yield, diastereoselectivity, and enantioselectivity. This methodology allows for the rapid synthesis of δ-lactams. Using this approach, we synthesized the pharmaceutically relevant piperidines paroxetine and femoxetine. A novel single-electron oxidation pathway for the N-heterocyclic carbene generated Breslow intermediate has been developed. Nitroarenes have been shown to transfer an oxygen from the nitro group to the β-position of an enal in an asymmetric fashion to generate β-hydroxy esters. This reaction affords desired β-hydroxy ester products in good yield and enantioselectivity and tolerates a wide range of enal substrates. A dimerization of aromatic enals to form 3,4-disubstituted cyclopentanones has been investigated. Using a single-electron oxidant, aromatic enals couple to form cyclopenanone products in good yield, good enantioselectivity, and excellent diastereoselectivity. A cross coupling has also been developed to afford non-symmetrical cyclopentanone products.born digitaldoctoral dissertationsengCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.asymmetriccarbenecatalysisorganicText