Date Approved

7-6-2026

Embargo Period

7-6-2026

Document Type

Thesis

Degree Name

M.S. Pharmaceutical Sciences

Department

Chemistry and Biochemistry

College

College of Science & Mathematics

Advisor

Gustavo Moura-Letts, Ph.D.

Committee Member 1

Subash Jonnalagadda, Ph.D.

Committee Member 2

Lark Perez, Ph.D.

Keywords

Catalysis;Oxaziridine;Transition Metal Catalysis

Abstract

Oxaziridines are versatile three-membered nitrogen–oxygen heterocycles that can function both as reactive intermediates and as components of transition-metal catalysts, enabling selective and diverse organic transformations. This work explores the dual role of oxaziridines in facilitating alkene functionalization and amide synthesis. We discovered that vanadooxaziridines catalyze intermolecular allylic amination with high regio- and chemoselectivity, providing a mild route to allylic amines, whereas molybdooxaziridine complexes display an unexpected preference for vinyl sulfonation, revealing a divergent pathway from the typical nitrogen-transfer reactions and offering access to synthetically valuable sulfur-containing motifs. In parallel, oxaziridine intermediates derived from imines mediate efficient formation of amides from aldehydes and amines, demonstrating their utility in constructing biologically relevant nitrogen-containing compounds. Collectively, these studies illustrate the unique capacity of oxaziridines to modulate reactivity, whether as ligated catalytic species or as transient intermediates, expanding the scope for selective functionalization and offering strategies relevant to complex molecule and pharmaceutical synthesis.

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