Abstract
Nonactivated aziridine with an electron-donating group at the ring nitrogen should be activated to an aziridinium ion prior to being converted to cyclic and acyclic nitrogen-containing molecules. This review describes ways to generate aziridinium ions and their utilization for synthetic purposes. Specifically, the intra- and intermolecular formation of aziridinium ions with proper electrophiles are classified, and their regio- and stereoselective transformations with nucleophiles are described on the basis of recent developments.
Highlights
Aziridines are three-membered cyclic organic heterocyclic compounds with one niAziridines are three-membered cyclic organic heterocyclic compounds with one nitrotrogen atom in the ring
Activated aziridines are quite reactive toward most nucleophiles, while nonactivated aziridines are inert unless they are activated as aziridinium ions or their equivalents by proper trimethylsilyl, and
This scheme showed that an azide nucleophile could drive the aziridine ring (24) with assistance of Lewis acid AlCl3 in aqueous medium to yield α-azido-β-aminopropionate (25) [50], which was utilized for the synthesis of natural product biemamide (B) (26) [51]
Summary
Aziridines are three-membered cyclic organic heterocyclic compounds with one niAziridines are three-membered cyclic organic heterocyclic compounds with one nitrotrogen atom in the ring They are valuable and versatile due to the reactive three-memgen atom in the ring. Ring-strained and aziridines, e.g., other various three-membered ring compounds pounds such as cyclopropane oxirane, render nitrogen-containing comsuch as cyclopropane and oxirane, renderwith various nitrogen-containing compounds through pounds through ring-opening reactions nucleophiles [10,11,12,13]. Their stabilring-opening reactions with [10,11,12,13].
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