Digitized Honors Theses (2002-2017)

Date of Award

5-2014

Document Type

Undergraduate Thesis

Degree Name

BS

Department

Biomedical Sciences

Faculty Mentor

David Forbes

Abstract

Recent developments such as high material costs and the emphasis on environmental concerns have made the development of alternative approaches a necessity. Furthermore, methods that promote reduced environmental load factor and atom economy while being synthetically versatile provide a significant advantage in drug synthesis. With the concept of sulfur ylide chemistries readily available, a novel method was developed to exploit the advantages of this approach toward modern, organic synthesis by tailoring the sulfur ylide moiety for each specific synthetic need. The research began by first examining the ability to construct a survey of sulfur ylide (S-ylide) precursors, with the goal being to determine each S-ylide precursor's rate of ylide formation and eventually, the application of the S-ylide to form cyclopropanes. Once a cyclopropanation protocol was generated from ylide formation experiment, we embarked on a cyclopropanation study. From the study, it was determined the oxidation of sulfur was critical in order for it to be an efficient methylene transfer agent. With this new information in hand, we synthesized a new S-ylide precursor, a sulfoximine, that has increased solubility in organic solvents, relatively cheap production, and chirality on the sulfur atom that is capable of being resolved. Further research is being performed to optimize this reagent as an efficient chiral methylene transfer agent.

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