An Inexpensive and Selective Oxygenation of N-Alkyl Imines to Oxaziridines

Abstract

A range of N-alkyl imines was oxidised to corresponding oxaziridines in a highly selective manner with sodium tungstate-30% H₂O₂ in acetonitrile under mild conditions.

Key words

imines - oxidation - oxaziridine - sodium tungstate - peroxide

References

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16

General Procedure.
To a solution of aldimine (1 mmol) in MeCN (5 mL) and sodium tungstate (10 mol%) was added 30% H₂O₂ (0.15 mL) dropwise at r.t. The progress of the reaction was monitored by TLC. After the completion of the reaction, the solvent was removed in vacuo, any excess H₂O₂ was quenched with sat. Na₂SO₃ solution and the product was re-extracted with CHCl₃. The solvent was dried over Na₂SO₄(anhyd) and evaporated. The crude product was purified by column chromatography on silica gel using mixtures of hexane and EtOAc.