A novel transformation of primary amines to N-monoalkylhydroxylamines

H. Tokuyama, T. Kuboyama, A. Amano, T. Yamashita, T. Fukuyama

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49 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1299-1304
Number of pages6
JournalSynthesis
Issue number9
Publication statusPublished - 2000 Sep 2
Externally publishedYes

Keywords

  • Amine
  • Cyanomethylation
  • Hydroxylamine
  • Nitrone
  • Oxidation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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  • Cite this

    Tokuyama, H., Kuboyama, T., Amano, A., Yamashita, T., & Fukuyama, T. (2000). A novel transformation of primary amines to N-monoalkylhydroxylamines. Synthesis, (9), 1299-1304.