A novel transformation of primary amines to N-monoalkylhydroxylamines

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

doi:10.1055/s-2000-6428

A novel transformation of primary amines to N-monoalkylhydroxylamines

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

PHA - Molecular Pharmaceutical Science

The University of Tokyo

Research output: Contribution to journal › Article › peer-review

56 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 language	English
Pages (from-to)	1299-1304
Number of pages	6
Journal	Synthesis
Issue number	9
DOIs	https://doi.org/10.1055/s-2000-6428
Publication status	Published - 2000

Keywords

Amine
Cyanomethylation
Hydroxylamine
Nitrone
Oxidation

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10.1055/s-2000-6428

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title = "A novel transformation of primary amines to N-monoalkylhydroxylamines",

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.",

keywords = "Amine, Cyanomethylation, Hydroxylamine, Nitrone, Oxidation",

author = "H. Tokuyama and T. Kuboyama and A. Amano and T. Yamashita and T. Fukuyama",

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doi = "10.1055/s-2000-6428",

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journal = "Synthesis",

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T1 - A novel transformation of primary amines to N-monoalkylhydroxylamines

AU - Tokuyama, H.

AU - Kuboyama, T.

AU - Amano, A.

AU - Yamashita, T.

AU - Fukuyama, T.

PY - 2000

Y1 - 2000

N2 - 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.

AB - 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.

KW - Amine

KW - Cyanomethylation

KW - Hydroxylamine

KW - Nitrone

KW - Oxidation

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DO - 10.1055/s-2000-6428

M3 - Article

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SP - 1299

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JO - Synthesis

JF - Synthesis

IS - 9

ER -

A novel transformation of primary amines to N-monoalkylhydroxylamines

Abstract

Keywords

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