Graduation Year

2024

Document Type

Campus Only Senior Thesis

Degree Name

Bachelor of Arts

Department

Chemistry

Reader 1

Nicholas Ball

Reader 2

Thomas Vasquez

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Terms of Use for work posted in Scholarship@Claremont.

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© 2024 Natalie Schur

Abstract

Phosphorus(V)-fluorides have been synthesized since the 1930s, initially for agricultural purposes, but also repurposed as chemical weapons. Despite a dark history, they also serve as pharmaceutical drugs like DFP, used for treating glaucoma1. In the past few years, innovations with phosphorus(V)- fluorides have been made in drug discovery, biotechnology, and carbon capture. The untapped potential of organophosphate compounds can be achieved through novel synthetic pathways. In 2023, the Sharpless group stimulated P(V) chemistry by developing the Phosphorus(V)-Fluoride Exchange (PFEx) reaction, which offers a new avenue to organophosphates with improved stability compared to previous methods2. However, due to the cholinergic properties of phosphorus(V)- fluorides, these compounds can be dangerous to work with. In fact, chirality and substituents around the P(V) center strongly impact acetylcholinesterase binding and therefore affect the varying toxicities of organophosphates. Synthetic techniques that minimize contact with dangerous compounds will allow for further innovation and countless discoveries in phosphorus(V) chemistry. To harness the potential of P(V)-F compounds, this work proposes a stereospecific synthesis of chiral phosphorus(V)-fluorides with enantiomeric excess, followed by an enantioselective technique that forms chiral phosphoramides while maintaining optical activity. A synthetic process that targets an enantiomer with lower toxicity will have profound impacts on drug development and human health.

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