2H‐Azirines: Recent Progress in Synthesis and Applications

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(11)

Опубликована: Янв. 29, 2024

Abstract 2H ‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances the synthesis and functionalization of have been reported. Neber rearrangement, isomerization isoxazole, oxidation enamine, C−H bond activation, decomposition vinyl azide, alkyne, multi‐step developed for efficient assembly ‐azirines. As versatile highly strained unsaturated heterocycles, ‐azirines can be used as distinctive building blocks towards significant functional groups, attracted extensive attention fabrication numerous heterocycles. Recent studies focused on [3+n] ring‐expansion reactions, nucleophilic addition C=N double or continuous followed by cyclization, ring‐opening to acyclic compounds, substitution sp 3 ‐C−H One most critical challenges is seeking a selective opening specific three bonds azirine circle, some what achieved basis metal catalyst, photocatalysis, combination catalyst photocatalysis. In this review, recent involving reactivity accompanied with breakthroughs summarized. The review mainly covers period from 2019 2023.

Язык: Английский

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Enantioselective Pd- and Cu-Catalyzed Hydrofunctionalization of Methylenecyclopropanes via a Distal C–C Bond Cleavage

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

The enantioselective ring-opening reactions of methylenecyclopropanes (MCPs) involving C–C bond activation via oxidative addition transition metals have been rarely reported. Here, we disclose a Pd/Cu-catalyzed enantio- and regioselective coupling between cyclic imino esters MCPs to produce α-allylated 2H-pyrrole derivatives. In this reaction, azomethine ylide formed by chiral copper catalyst with ketimine ester would serve as nucleophile react activated palladium catalysis. This bimetallic system exhibited broad substrate scope high regio- enantioselectivities.

Язык: Английский

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Substituted 2H-azirine derivatives - Versatile reagents to access skeletal diversity

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 142148 - 142148

Опубликована: Март 1, 2025

Язык: Английский

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Transition‐Metal Catalyzed Enantioselective Aziridination Reaction: Recent Development in Catalysis and Future Perspectives

ChemCatChem, Год журнала: 2024, Номер 16(21)

Опубликована: Июль 16, 2024

Abstract Chiral aziridines are important motifs in natural products and biologically significant compounds, as well one of the most valuable versatile building blocks for construction diverse chiral functionalized amines. Because importance aziridines, various novel transition‐metal‐based catalytic systems synthetic strategies have been established to investigate highly effective enantioselective aziridination process. This review outlined recent advances made transition‐metal catalyzed reactions, challenges potential field at current stage.

Язык: Английский

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Synthetic Approaches for the Construction of Chiral Aziridines

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 30, 2024

Abstract 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, materials both academic industrial communities. Recent years witnessed broad spectrum prominent breakthroughs the field chiral due to aziridine‐based three‐dimensional pharmacophores, resulted streamlining drug discovery process. Over past few decades, particular attention has been directed towards strategically efficient, versatile, practical assembly optically aziridines. These synthesis approaches great potential context construction pharmaceutical molecules, biologically pharmacologically relevant materials. In this review, several strategies for are summarized, could be divided into five categories: (1) Introduction; (2) Construction via reactions olefines with nitrene sources; (3) imines carbenes; (4) reaction azirines; (5) intramolecular cyclization amine derivatives.

Язык: Английский

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Three-membered ring systems

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 41 - 58

Опубликована: Янв. 1, 2024

Язык: Английский

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