Oxidative C–N Bond Cleavage of Cyclic Amines with Ammonium Hypochlorite

Yuya Kaieda; Kosuke Yamamoto; Hiroyuki Toguchi; Natsumi Hanazawa; Masami Kuriyama; Osamu Onomura

doi:10.1055/a-2062-8680

Synthesis, Table of Contents

Synthesis 2024; 56(10): 1576-1584
DOI: 10.1055/a-2062-8680

paper

C–H Bond Functionalization of Heterocycles

Oxidative C–N Bond Cleavage of Cyclic Amines with Ammonium Hypochlorite

Yuya Kaieda

^aGraduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan

,

Kosuke Yamamoto

^aGraduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan

,

Hiroyuki Toguchi

^aGraduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan

,

Natsumi Hanazawa

^aGraduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan

^bTsukuba Research Laboratories, Tokuyama Corporation, 40 Wadai, Tsukuba, Ibaraki 300-4247, Japan

,

Masami Kuriyama

^aGraduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan

,

Osamu Onomura ∗

^aGraduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan

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Abstract

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Abstract

An oxidative C–N bond cleavage of cyclic amines has been developed under metal-free conditions, providing N-Cl-ω-amino acids in moderate to excellent yields. The reactions proceed by using tetramethylammonium hypochlorite (TMAOCl) as an oxidant even on a gram scale. Hofmann–Löffler–Freytag-type reaction of N-Cl-ω-amino acids to form cyclic amino acids has also been demonstrated.

Key words

C–N bond cleavage - oxidation - cyclic amines - ammonium hypochlorite - amino acids

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References

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