Conjugation Studies: The Synthesis of Vinyl Aziridines through the aza-Darzens Reaction

Abstract

Aziridines, three membered heterocycles containing a nitrogen in the ring, are extremely valuable to synthetic organic chemistry, as subjecting these compounds to ring opening processes initiates further capabilities for the molecule. Additionally, aziridines themselves possess the capacity and characteristics suitable for pharmaceutical applications, increasing the interest and appeal for their synthesis. One of the approaches to the formation of these products is the aza-Darzens reaction between imines and brominated nucleophiles. The research presented here aims to analyze this technique, specifically between tert-butanesulfinimines and methyl (E)-4-bromo-3-methylbut-2-enoate. Within the context of the reaction mechanism, the pivotal step involves nitrogen on a sulfinimine enolate bonding to the gamma carbon of the nucleophile, effectively cleaving bromine and producing an aziridine. Investigation into the development of the aforementioned imines and nucleophile is also accomplished in this undertaking.