Synthetic Approaches for the Construction of Chiral Aziridines

• Published in: European journal of organic chemistry 2024-11, Vol.28 (2), p.n/a
• Main Authors: Liu, Qing‐Hui, Liu, Jiaxuan, Han, Ya‐Ping, Liang, Yong‐Min, Peng, Li‐Zeng
• Format: Article
• Language: English
• Subjects: Agrochemicals; Assembly; Chemical synthesis; Construction; Construction of optically active aziridines via intramolecular cyclization of amine; Construction of optically active aziridines via reaction of azirines; Functional materials; Heterocyclic compounds; Imines; Natural products; Optical activity; Optically active aziridines; Pharmaceuticals; Reactions of imines with carbenes; Reactions of olefines with nitrene sources
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202401048

Optically active aziridines represent a pivotal class of rigid three‐membered nitrogen‐heterocyclic compounds found in natural products, pharmaceuticals, agrochemicals, and functional motifs, which have demonstrated outstanding practicability as therapeutic molecular frameworks, versatile synthetic endpoints, and functional materials in both academic and industrial communities. Recent years have witnessed a broad spectrum of prominent breakthroughs in the field of chiral aziridines due to the aziridine‐based rigid and three‐dimensional pharmacophores, which have resulted in streamlining the drug discovery process. Over the past few decades, particular attention has been directed towards the strategically efficient, versatile, and practical assembly of optically active aziridines. These synthesis approaches have demonstrated great potential in the context of the construction of pharmaceutical molecules, biologically and pharmacologically relevant natural products, and functional materials. In this review, several synthetic strategies for the assembly of chiral aziridines are summarized, which could be divided into five categories: (1) Introduction; (2) Construction of optically active aziridines via reactions of olefines with nitrene sources; (3) Construction of optically active aziridines via reactions of imines with carbenes; (4) Construction of optically active aziridines via reaction of azirines; (5) Construction of optically active aziridines via intramolecular cyclization of amine derivatives. Optically active aziridines represent an important class of rigid three‐membered nitrogen‐heterocyclics because they are privileged structural frameworks in biologically and pharmacologically relevant natural products. This review is to summarize complementary assembly of optically active aziridines in recent years, as well as their applications in the agrochemical and pharmaceutical industry.