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Diastereoselective Alkylations of Monoxidized Organosulfur Species and Associated Reactivity of Amino Iodides

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Title: Diastereoselective Alkylations of Monoxidized Organosulfur Species and Associated Reactivity of Amino Iodides
Author: Sammons, Scott
Department: Department of Chemistry
Program: Chemistry
Advisor: Schwan, Adrian
Abstract: Organosulfur species are prevalent and bountiful through nature, biological systems, and pharmaceutical compounds. The chemistry presented herein explores synthetic transformations of organosulfur species to evaluate accessibility and diastereomeric ratios. Chapter 1 explores β-amino iodide systems and their associated reactivity patterns in attempting to access biologically active ant venom alkaloids. Creative reaction pathways were introduced in an endeavour to expedite the synthesis previously seen for these compounds. Chapter 2 focuses on the diastereomeric ratios produced from alkylations of sulfenate species. Density Functional Theory (DFT) was employed to predict that altering the protecting group (PG) from a Boc to a trifluoroacetyl resulted in a different stabilization conformation for the transition state. N-C(O)CF3 sulfoxides were synthesized through sulfenate releases and compared to previously generated N-Boc sulfoxides to see if inversion of stereochemistry prevailed upon changing the PG.
URI: https://hdl.handle.net/10214/25766
Date: 2021-05
Rights: Attribution 4.0 International
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Attribution 4.0 International Except where otherwise noted, this item's license is described as Attribution 4.0 International