A Review on Recent Advances in the Synthesis of Aziridines and their Applications in Organic Synthesis

Abstract

: Aziridines are the saturated three-membered cyclic amines that constitute an important group of synthetic intermediates. These could act as a precursor for diverse organic compounds owing to the reactivity due to the ring strain associated with them. The outstanding property of aziridines is their high reactivity towards various nucleophilic and electrophilic reagents to acquire more stable ring-opened or ring-expanded amines that could be obtained from the release of strain energy intrinsic in a small ring. As such, aziridines could be used in the synthesis of 4-7 membered heterocycles of biological and industrial significance, such as azetidines, imidazoles, thiazoles, pyrazines, pyrimidines, benzothiazines, benzodiazepines, etc. Earlier synthesis of aziridines was considered a laborious task due to their instability. However, various synthetic approaches leading to the formation of aziridines are now available in the literature. Recently, green, cost-effective and approaches based on simpler work-up for these reactions have attracted researcher's attention. This review article deals with synthetic routes of aziridines and aziridine applications in organic synthesis.

Substrate-Directed Enantioselective Aziridination of Alkenyl Alcohols Controlled by a Chiral Cation

“…A powerful array of catalytic asymmetric protocols exists for this transformation, and as a result, retrosynthesis to a chiral epoxide is frequently a key disconnection when planning an asymmetric synthesis . Given the similar prevalence of nitrogen atoms in molecules of societal importance, alkene aziridination has the potential to be equally enabling, and great advances have been made in intermolecular asymmetric aziridination over the past three decades (Figure a) . Olefins conjugated with electron-withdrawing groups were the first to be subjected to the asymmetric transformation, as in Evans’ aziridination of cinnamate esters using copper-bis­(oxazoline) complexes .…”

Recent advances in the accessibility, synthetic utility, and biological applications of aziridines

“…We have focused our attention on the past three years, trying to describe the most important breakthroughs that have been made after the publication of other reviews covering this field. 5…”

Electrochemical flow aziridination of unactivated alkenes

“…To achieve this goal, we considered recent advances in aziridine synthesis. Catalytic alkene aziridination is one of the most efficient routes to producing aziridines using fundamental feedstocks—alkenes and amines [ 15 , 16 ]. To date, four strategies have been well established for realizing alkene aziridination (Fig.…”