Asymmetric Synthesis and Oxidation with Oxaziridines

Oxaziridines, three-membered heterocycles bearing a nitrogen–oxygen bond, have emerged as versatile reagents for stereocontrolled oxidation and nitrogen‐transfer processes. Their unique combination of ring strain and electronic properties enables selective oxygen transfer to a broad range of substrates, including enolates, sulfides and imines, often under mild conditions. In asymmetric synthesis, chiral oxaziridine scaffolds or catalytic systems generate high levels of enantioselectivity, unlocking access to valuable chiral alcohols, epoxides and amino alcohols. Advances in catalyst design—encompassing chiral Lewis acids, organocatalysts and enzyme‐mimetic frameworks—have expanded the scope of enantioselective oxidations, enabling scalable routes to pharmaceutically relevant intermediates. The inherent tunability of oxaziridine N‐substituents has further allowed fine‐tuning of reactivity and selectivity, while the development of greener oxidant systems has reduced environmental impact, aligning with contemporary sustainable chemistry goals.

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Asymmetric Synthesis and Oxidation with Oxaziridines publication trend

The graph below shows the total number of articles in asymmetric synthesis and oxidation with oxaziridines across all publications each year (not limited to Nature Index journals).

Technical terms

Oxaziridine: A three-membered ring containing adjacent nitrogen and oxygen atoms; used as an electrophilic oxidant or nitrogen donor in organic synthesis.

Asymmetric synthesis: A strategy to construct molecules in which one enantiomer is formed preferentially over the other, achieving high enantioselectivity.

Enantioselectivity: The preference for the formation of one mirror‐image isomer (enantiomer) over the other in a chemical reaction, usually expressed as enantiomeric excess.

Oxygen‐transfer agent: A reagent that delivers an oxygen atom to a substrate, facilitating oxidation reactions under mild conditions.

Organocatalyst: A small organic molecule that accelerates a reaction and controls stereochemistry without the need for metal centres.

References

1. Hydrogen peroxide/dimethyl carbonate: a green system for epoxidation of N -alkylimines and N -sulfonylimines. One-pot synthesis of N -alkyloxaziridines from N -alkylamines and (hetero)aromatic aldehydes. Green Chemistry (2016).
2. Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines. Molecules (2018).