Graduation Term
2024
Degree Name
Master of Science (MS)
Department
Department of Chemistry
Committee Chair
Timothy A Mitchell
Abstract
Cycloadditions are capable of producing multiple bonds in a single step with excellent atom economy, and they are well suited to generate a great deal of complexity in one step. Cycloadditions can transform mostly linear molecules into three dimensional molecules, which is incredibly important for drug synthesis. The Mitchell group research has revolved around uncovering the mechanisms involved in silyloxypyrone (5+2) cycloadditions. An improved understanding of the reactivity of silyloxypyone (5+2) cycloadditions has allowed for more efficient exploration of techniques to improve the utility of (5+2) cycloadditions and the complexity of cycloadducts. Tethers are utilized to provide stereochemical and entropic control of cycloaddition reactions. Cleavable tethers allow for these benefits while also allowing the tether region to be modified after the cycloaddition occurs. We have previously investigated DABO tethers as potentially cleavable tethers, which were unfortunately far less labile than desired. This work explores a variety of tethers employing boron reagents (i.e. B-N, B-O, and B-F interactions) that may allow for cleavable tethers with a greater level of utility than previous examples of cleavable tethers. A tandem Petasis (5+2) cycloaddition reaction was also explored. This method produces a traceless boron tether and allows the construction of unique tethers to improve customizability of amine-containing tethers.
Access Type
Thesis-Open Access
Recommended Citation
Corrie, Seth Ian, "Utilizing B-n, B-o, and B-f Interactions toward Novel ( 5+2 ) Cycloadditions" (2024). Theses and Dissertations. 1971.
https://ir.library.illinoisstate.edu/etd/1971
DOI
https://doi.org/10.30707/ETD2024.20240827063556636622.999992