Carbamate as an accelerating group in intermolecular Pauson-Khand reaction

Shota Asano; Kaori Itto-Nakama; Hirokazu Arimoto

doi:10.1016/j.tetlet.2020.151974

Carbamate as an accelerating group in intermolecular Pauson-Khand reaction

Shota Asano, Kaori Itto-Nakama, Hirokazu Arimoto

LIF - Molecular and Chemical Life Science

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

2 Citations (Scopus)

Abstract

The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl O-allyl carbamate with alkyne-cobalt complex gave cyclopentenones in high yield (up to 90%) and regioselectivity (>9:1).

Original language	English
Article number	151974
Journal	Tetrahedron Letters
Volume	61
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2020.151974
Publication status	Published - 2020 Jun 11

Keywords

Accelerating group
Carbamate
Cyclopentenone
Intermolecular
Pauson-Khand reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2020.151974

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title = "Carbamate as an accelerating group in intermolecular Pauson-Khand reaction",

abstract = "The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl O-allyl carbamate with alkyne-cobalt complex gave cyclopentenones in high yield (up to 90%) and regioselectivity (>9:1).",

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AU - Asano, Shota

AU - Itto-Nakama, Kaori

AU - Arimoto, Hirokazu

PY - 2020/6/11

Y1 - 2020/6/11

N2 - The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl O-allyl carbamate with alkyne-cobalt complex gave cyclopentenones in high yield (up to 90%) and regioselectivity (>9:1).

AB - The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl O-allyl carbamate with alkyne-cobalt complex gave cyclopentenones in high yield (up to 90%) and regioselectivity (>9:1).

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KW - Cyclopentenone

KW - Intermolecular

KW - Pauson-Khand reaction

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Carbamate as an accelerating group in intermolecular Pauson-Khand reaction

Abstract

Keywords

ASJC Scopus subject areas

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