Nitrone Chemistry and Organic Synthesis
Summary
Nitrones are aza-oxy ylides characterised by a C=N⁺–O⁻ motif, which behave as versatile 1,3-dipoles in organic synthesis. Their polarised electronic structure enables cycloaddition with alkenes and alkynes to furnish isoxazolidine scaffolds, which can thereafter undergo reductive or thermal N–O bond cleavage to reveal densely functionalised amines and homoallylic alcohols. Beyond cycloaddition, nitrones serve as radical spin traps in mechanistic studies of oxidative stress, stabilising transient radicals as persistent nitroxide adducts. Recent advances have extended their scope to metal-free oxidations of secondary amines, domino condensations generating cyclic nitrones in situ, and asymmetric variants that impart high enantiocontrol in heterocycle synthesis. These developments have underpinned streamlined routes to complex alkaloids, bioactive molecules and functional materials, while also addressing sustainability through greener reagents and continuous-flow processes.
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Nitrone Chemistry and Organic Synthesis publication trend
The graph below shows the total number of articles in nitrone chemistry and organic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Nitrone: A dipolar species featuring a C=N⁺–O⁻ functionality capable of both cycloaddition and radical-trapping reactions.
1,3-Dipolar cycloaddition: A pericyclic reaction between a 1,3-dipole (e.g. nitrone) and a dipolarophile (alkene or alkyne) that forms five-membered heterocycles.
Dipolarophile: An unsaturated compound (alkene or alkyne) that reacts with a 1,3-dipole to undergo cycloaddition.
Isoxazolidine: A saturated five-membered heterocycle containing adjacent nitrogen and oxygen atoms, typically produced by nitrone cycloaddition.
References
- Intramolecular cycloaddition of nitrones in total synthesis of natural products. Natural Product Reports (2025).
- Characterization of the Radical Trapping Activity of a Novel Series of Cyclic Nitrone Spin Traps (∗). Journal of Biological Chemistry (1996).
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