A Study into the Design, Synthesis, and Application of Asymmetric Catalyst Systems
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Benda, Meghan
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Abstract
The importance of asymmetry, or chirality, in the natural world cannot be overstated and its role has been extensively studied in the fields of chemistry, biology, physics, materials and more. As a result, researchers have dedicated immense time, resources, and funding to the development of chiral resolution and asymmetric induction techniques. In this thesis, we focus on the design, synthesis, and applications of asymmetric catalyst systems. First, in a demonstration of the utility of asymmetric catalysis in the production of medicinally relevant materials, we disclose the total synthesis of three 7-keto-9-hydroxy-8,4’-oxyneolignans in up to >99% ee featuring a key Sharpless asymmetric dihydroxylation step. Additionally, we disclose the synthesis and reactivity of a pair of C2-symmetric thiophene-fused cyclopentadienyl ferrocenes. Finally, the attempted formation of a binaphthyl-based chiral calcium disulfonimide complex is discussed including its observed reactivity toward ring-opening cyclizations.
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Date
2023-04-17
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Dissertation