, volume 57 , issue 29 , pages 3599-3602

A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan

Yanshun Zhang ^{1, 2, 3, 4, 5, 6}

尹维 Wei Yin ⁷

Wei Yin ^{8, 9, 10, 11, 12}

Min Shi ^{1, 2, 3, 4, 5, 6, 7}

Hide authors affiliations Show authors affiliations: 12 affiliations

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People's Republic of China |

Key Laboratory for Advanced Materials and Institute of Fine Chemicals

School of Chemistry & Molecular Engineering

⁴

East China University of Science and technology |

⁵

Shanghai 200237 |

⁶

People's Republic of China |

⁷

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

University of Chinese Academy of Sciences

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

⁸

State Key Laboratory of Organometallic Chemistry

⁹

Center for Excellence in Molecular Synthesis

¹⁰

University of Chinese Academy of Sciences |

¹¹

Shanghai Institute of Organic Chemistry |

¹²

Chinese Academy of sciences

Publication type: Journal Article

Publication date: 2021-03-08

Royal Society of Chemistry (RSC)

Chemical Communications

scimago Q1

wos Q2

SJR: 1.037

CiteScore: 7.4

Impact factor: 4.2

ISSN: 13597345, 1364548X

DOI: 10.1039/d1cc00707f

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PubMed ID: 33710234

Materials Chemistry

Metals and Alloys

Surfaces, Coatings and Films

General Chemistry

Ceramics and Composites

Electronic, Optical and Magnetic Materials

Catalysis

Abstract

A silver-catalyzed diastereoselective one-pot domino cyclization-migration/inverse electron-demand oxo-Diels–Alder reaction has been disclosed in this communication through the in situ generated cyclobutane-fused furan intermediate with 4-vinyl-2,3-dioxopyrrolidine for the construction of 2-oxopyrrolidine-fused tricyclic compounds in moderate to good yields with a broad substrate scope under mild conditions. This new synthetic protocol features good efficiency and atom- and step-economy. A plausible reaction mechanism has also been proposed on the basis of previous reports, NMR tracing and control experiments.

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GOST |

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GOST Copy

Zhang Y. et al. A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan // Chemical Communications. 2021. Vol. 57. No. 29. pp. 3599-3602.

GOST all authors (up to 50) Copy

Zhang Y., Wei Yin 尹., Yin W., Shi M. A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan // Chemical Communications. 2021. Vol. 57. No. 29. pp. 3599-3602.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/d1cc00707f

UR - https://xlink.rsc.org/?DOI=D1CC00707F

TI - A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan

T2 - Chemical Communications

AU - Zhang, Yanshun

AU - Wei Yin, 尹维

AU - Yin, Wei

AU - Shi, Min

PY - 2021

DA - 2021/03/08

PB - Royal Society of Chemistry (RSC)

SP - 3599-3602

IS - 29

VL - 57

PMID - 33710234

SN - 1359-7345

SN - 1364-548X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2021_Zhang,

author = {Yanshun Zhang and 尹维 Wei Yin and Wei Yin and Min Shi},

title = {A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan},

journal = {Chemical Communications},

year = {2021},

volume = {57},

publisher = {Royal Society of Chemistry (RSC)},

month = {mar},

url = {https://xlink.rsc.org/?DOI=D1CC00707F},

number = {29},

pages = {3599--3602},

doi = {10.1039/d1cc00707f}

}

MLA

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MLA Copy

Zhang, Yanshun, et al. “A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan.” Chemical Communications, vol. 57, no. 29, Mar. 2021, pp. 3599-3602. https://xlink.rsc.org/?DOI=D1CC00707F.

Publisher

Royal Society of Chemistry (RSC)

Journal

Chemical Communications

scimago Q1

wos Q2

SJR

1.037

CiteScore

7.4

Impact factor

4.2

ISSN

13597345 (Print)

1364548X (Electronic)