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A Novel Transformation of Primary Amines to N-Monoalkylhydroxylamines
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2000
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M-cpba OxidationEngineeringOrganic ChemistryCatalysisSynthetic ChemistryChemistryHeterocycle ChemistryStereoselective SynthesisNovel TransformationEnantioselective SynthesisBiomolecular EngineeringSelective Mono-cyanomethylation
A novel transformation of primary amines to the corresponding N-monoalkylhydroxylamines is described. The three-step protocol involves selective mono-cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamine hydrochloride. The method is applicable for a wide range of primary amines, including alkyl, benzyl, and chiral.