Graduation Year

2026

Document Type

Campus Only Senior Thesis

Degree Name

Bachelor of Arts

Department

Chemistry

Reader 1

Dr. Nicholas D. Ball

Reader 2

Daniel Wellman

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Terms of Use for work posted in Scholarship@Claremont.

Abstract

Sulfonimidoyl fluorides have emerged as promising chiral sulfur(VI) electrophiles that combine the modularity of sulfur-fluoride exchange (SuFEx) chemistry with a configurationally stable, stereogenic sulfur center. Despite recent advances in enantioenriched S(VI) synthesis, practical methods for the asymmetric synthesis of sulfoximines remain limited by multistep procedures and the reliance on harsh or moisture-sensitive reagents. This work investigates Boc-protected sulfonimidoyl fluorides as modular precursors for a streamlined, Lewis acid-mediated route to sulfoximines under operationally mild conditions. Building on Ca(NTf2)/ DABCO activation platforms for S(VI)-F substitution, we evaluate the role of calcium coordination in enhancing electrophilic activation and promoting selective phenolic coupling. To achieve enantioselective control at the sulfur, we have tested N,N’-dioxide Feng ligands as chiral oxygen-donor frameworks that form C2-symmetric metal complexes. These ligands combine conformational adaptability with intramolecular hydrogen-bonding to create a pocket around the metal center, controlling nucleophilic attack at the sulfur atom. Through characterization studies and synthetic optimization, we have established a safe, affordable, and enantioselective route to sulfoximines that minimizes purification steps and avoids hazardous lithium-based reagents. Future work will investigate the scope of chiral ligands to improve enantiocontrol and synthesize other biologically active, pharmaceutically relevant S(VI) compounds.

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