Recent advances in the application of contiguously functionalized aziridines for the synthesis of pharmaceutical precursors via regioselective ring-opening reactions

• A synthetic breakthrough for the construction of contiguously functionalized aziridines , including epoxyaziridines, bisaziridines, and cyclopropylaziridines. • Contiguously functionalized aziridines serve as powerful and versatile tools for synthesizing pharmaceutical precursors because of their unique reactivity profiles. • This approach emphasizes the strategic design and synthesis of contiguous aziridine-based compounds, enabling regioselective and stereoselective ring-opening reactions. • These ring-opening reactions facilitate the construction of diverse nitrogen-containing scaffolds that are essential for the synthesis of bioactive compound. • Well-designed aziridine-based (hetero)cycles offer potentially adaptable routes for advancing synthetic methodologies for drug discovery and bioactive molecule design. Contiguously functionalized aziridines, including epoxyaziridines, bisaziridines, and cyclopropylaziridines, are valuable intermediates in the synthesis of medicinally relevant compounds owing to their distinctive reactivity and structural versatility. This review explores strategic routes for the synthesis and application of these three-membered (hetero)cyclic systems, highlighting how their regioselective ring-opening reactions (RORs) facilitate the formation of diverse nitrogen-containing scaffolds. By focusing on the design and functionalization of contiguous aziridines, we demonstrated their utility in constructing complex chiral frameworks and bioactive moieties, such as those found in antibiotics, antifungal agents, and other pharmacologically significant molecules. The unique reactivity of aziridine-based systems enables selective transformations that enhance both synthetic efficiency and stereocontrol, offering flexible pathways for the development of therapeutically relevant compounds. This review emphasizes the recent advancements in the regioselective functionalization of aziridine-based (hetero)cycles, underscoring their potential to drive innovation in medicinal chemistry and drug discovery.

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Publication Details

Journal
Molecular Catalysis
Published
2025-02-26
DOI
https://doi.org/10.1016/j.mcat.2025.114943
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Recent advances in the application of contiguously functionalized aziridines for the synthesis of pharmaceutical precursors via regioselective ring-opening reactions

Jung Woon Yang, Huimyoung Byeon, Hyun‐Joon Ha
Molecular Catalysis
Synthesis and Catalytic Reactions
article

Recent advances in the application of contiguously functionalized aziridines for the synthesis of pharmaceutical precursors via regioselective ring-opening reactions

Jung Woon Yang, Huimyoung Byeon, Hyun‐Joon Ha
article en

Abstract

• A synthetic breakthrough for the construction of contiguously functionalized aziridines , including epoxyaziridines, bisaziridines, and cyclopropylaziridines. • Contiguously functionalized aziridines serve as powerful and versatile tools for synthesizing pharmaceutical precursors because of their unique reactivity profiles. • This approach emphasizes the strategic design and synthesis of contiguous aziridine-based compounds, enabling regioselective and stereoselective ring-opening reactions. • These ring-opening reactions facilitate the construction of diverse nitrogen-containing scaffolds that are essential for the synthesis of bioactive compound. • Well-designed aziridine-based (hetero)cycles offer potentially adaptable routes for advancing synthetic methodologies for drug discovery and bioactive molecule design. Contiguously functionalized aziridines, including epoxyaziridines, bisaziridines, and cyclopropylaziridines, are valuable intermediates in the synthesis of medicinally relevant compounds owing to their distinctive reactivity and structural versatility. This review explores strategic routes for the synthesis and application of these three-membered (hetero)cyclic systems, highlighting how their regioselective ring-opening reactions (RORs) facilitate the formation of diverse nitrogen-containing scaffolds. By focusing on the design and functionalization of contiguous aziridines, we demonstrated their utility in constructing complex chiral frameworks and bioactive moieties, such as those found in antibiotics, antifungal agents, and other pharmacologically significant molecules. The unique reactivity of aziridine-based systems enables selective transformations that enhance both synthetic efficiency and stereocontrol, offering flexible pathways for the development of therapeutically relevant compounds. This review emphasizes the recent advancements in the regioselective functionalization of aziridine-based (hetero)cycles, underscoring their potential to drive innovation in medicinal chemistry and drug discovery.

Molecular CatalysisVol. 576
Hankuk University of Foreign Studies (KR), Sungkyunkwan University (KR)
Openalex Percentile: Top 97%
Synthesis and Catalytic Reactions
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