Efficient and Environmentally Benign Oxidative Cleavage of Pyrrolidine-2-methanols to γ-Lactams Using 2-Iodobenzamide as a Catalyst and Oxone

Hema Naga Lakshmi Perumalla; Tomoya Fujiwara; Maki Okada; Kanna Asakubo; Takashi Okitsu; Kengo Kasama; Hisanori Nambu; Takayuki Yakura

doi:10.1248/cpb.c23-00742

Efficient and Environmentally Benign Oxidative Cleavage of Pyrrolidine-2-methanols to γ-Lactams Using 2-Iodobenzamide as a Catalyst and Oxone

Hema Naga Lakshmi Perumalla, Tomoya Fujiwara, Maki Okada, Kanna Asakubo, Takashi Okitsu, Kengo Kasama, Hisanori Nambu, Takayuki Yakura^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

Abstract

The oxidative cleavage reaction of pyrrolidine-2-methanols to γ-lactams has been described. In this reaction, [4-iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid and powdered Oxone (2KHSO₅·KHSO₄·K₂SO₄) were employed as the catalyst and co-oxidant, respectively. The reaction is efficient and environmentally benign because it produces various lactams from readily available substrates in moderate to excellent yields using organocatalyst and inorganic non-toxic co-oxidant.

Original language	English
Pages (from-to)	75-79
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	72
Issue number	1
DOIs	https://doi.org/10.1248/cpb.c23-00742
State	Published - 2024/01/01

Keywords

Oxone
environmentally benign oxidation
hypervalent iodine
lactam
oxidative cleavage

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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10.1248/cpb.c23-00742

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title = "Efficient and Environmentally Benign Oxidative Cleavage of Pyrrolidine-2-methanols to γ-Lactams Using 2-Iodobenzamide as a Catalyst and Oxone",

abstract = "The oxidative cleavage reaction of pyrrolidine-2-methanols to γ-lactams has been described. In this reaction, [4-iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid and powdered Oxone (2KHSO5·KHSO4·K2SO4) were employed as the catalyst and co-oxidant, respectively. The reaction is efficient and environmentally benign because it produces various lactams from readily available substrates in moderate to excellent yields using organocatalyst and inorganic non-toxic co-oxidant.",

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author = "Perumalla, {Hema Naga Lakshmi} and Tomoya Fujiwara and Maki Okada and Kanna Asakubo and Takashi Okitsu and Kengo Kasama and Hisanori Nambu and Takayuki Yakura",

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doi = "10.1248/cpb.c23-00742",

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AU - Perumalla, Hema Naga Lakshmi

AU - Fujiwara, Tomoya

AU - Okada, Maki

AU - Asakubo, Kanna

AU - Okitsu, Takashi

AU - Kasama, Kengo

AU - Nambu, Hisanori

AU - Yakura, Takayuki

PY - 2024/1/1

Y1 - 2024/1/1

N2 - The oxidative cleavage reaction of pyrrolidine-2-methanols to γ-lactams has been described. In this reaction, [4-iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid and powdered Oxone (2KHSO5·KHSO4·K2SO4) were employed as the catalyst and co-oxidant, respectively. The reaction is efficient and environmentally benign because it produces various lactams from readily available substrates in moderate to excellent yields using organocatalyst and inorganic non-toxic co-oxidant.

AB - The oxidative cleavage reaction of pyrrolidine-2-methanols to γ-lactams has been described. In this reaction, [4-iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid and powdered Oxone (2KHSO5·KHSO4·K2SO4) were employed as the catalyst and co-oxidant, respectively. The reaction is efficient and environmentally benign because it produces various lactams from readily available substrates in moderate to excellent yields using organocatalyst and inorganic non-toxic co-oxidant.

KW - Oxone

KW - environmentally benign oxidation

KW - hypervalent iodine

KW - lactam

KW - oxidative cleavage

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U2 - 10.1248/cpb.c23-00742

DO - 10.1248/cpb.c23-00742

M3 - 学術論文

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AN - SCOPUS:85182956576

SN - 0009-2363

VL - 72

SP - 75

EP - 79

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

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Efficient and Environmentally Benign Oxidative Cleavage of Pyrrolidine-2-methanols to γ-Lactams Using 2-Iodobenzamide as a Catalyst and Oxone

Abstract

Keywords

ASJC Scopus subject areas

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