Diastereoselective Alkylations of Monoxidized Organosulfur Species and Associated Reactivity of Amino Iodides
- Resource Type
- Authors
- Sammons, Scott
- Source
- Subject
- Chemistry
Synthesis
Organic
Computational
Diastereomer
Asymmetric
Heterocycle
Fluorine
Sulfenate
Chirality
Organosulfur
Sulfoxide
NMR
- Language
- English
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. Natural Sciences and Engineering Research Council (NSERC)