Copper-catalyzed multicomponent assembly of γ-butenolides via the interception of carbonyl ylides with iminium ions

Mengchu Zhang; Sifan Yu; Ruyu Hua; Dan Zhang; Huang Qiu; Wenhao Hu

doi:10.1039/d2ob02075k

Copper-catalyzed multicomponent assembly of γ-butenolides via the interception of carbonyl ylides with iminium ions

Mengchu Zhang
, Sifan Yu
, Ruyu Hua
, Dan Zhang^*
, Huang Qiu^*
, Wenhao Hu^*

^*Corresponding author for this work

Chinese Medicine - Teaching and Research Division

Research output: Contribution to journal › Journal article › peer-review

3 Citations (Scopus)

Abstract

A Cu(I)-catalyzed three-component reaction of cyclopropenes, enamines and aldehydes has been realized. This reaction proceeds via the interception of carbonyl oxonium ylide intermediates with α, β-unsaturated iminium ions that are in situ generated from enamines and aldehydes under the catalysis of Cu(MeCN)₄PF₆, leading to the desired γ-butenolide derivatives in good yields and with moderate diastereoselectivities. Access to these derivatives with tethered ketone and alkynal groups will expand the structural diversity of multi-substituted butenolides.

Original language	English
Pages (from-to)	783-788
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	21
Issue number	4
Early online date	20 Dec 2022
DOIs	https://doi.org/10.1039/d2ob02075k
Publication status	Published - 28 Jan 2023

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@article{5d80c57a64d44772935ae5daaa0d04f3,

title = "Copper-catalyzed multicomponent assembly of γ-butenolides via the interception of carbonyl ylides with iminium ions",

abstract = "A Cu(I)-catalyzed three-component reaction of cyclopropenes, enamines and aldehydes has been realized. This reaction proceeds via the interception of carbonyl oxonium ylide intermediates with α, β-unsaturated iminium ions that are in situ generated from enamines and aldehydes under the catalysis of Cu(MeCN)4PF6, leading to the desired γ-butenolide derivatives in good yields and with moderate diastereoselectivities. Access to these derivatives with tethered ketone and alkynal groups will expand the structural diversity of multi-substituted butenolides.",

author = "Mengchu Zhang and Sifan Yu and Ruyu Hua and Dan Zhang and Huang Qiu and Wenhao Hu",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2023. Funding Information: We thank Kuiyong Dong and Gengxin Liu for their help and suggestion in completing the project. Support for this research from the National Natural Science Foundation of China (81973176, 21901259, 22171294, and 92056201), the Guangdong Innovative and Entrepreneurial Research Team Program (2016ZT06Y337), the Guangdong Provincial Key Laboratory of Chiral Molecule, and the Natural Science Foundation of Guangdong Province (2021A1515010401) and Drug Discovery (2019B030301005) is greatly acknowledged.",

year = "2023",

month = jan,

day = "28",

doi = "10.1039/d2ob02075k",

language = "English",

volume = "21",

pages = "783--788",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "4",

}

TY - JOUR

T1 - Copper-catalyzed multicomponent assembly of γ-butenolides via the interception of carbonyl ylides with iminium ions

AU - Zhang, Mengchu

AU - Yu, Sifan

AU - Hua, Ruyu

AU - Zhang, Dan

AU - Qiu, Huang

AU - Hu, Wenhao

N1 - Publisher Copyright: © The Royal Society of Chemistry 2023. Funding Information: We thank Kuiyong Dong and Gengxin Liu for their help and suggestion in completing the project. Support for this research from the National Natural Science Foundation of China (81973176, 21901259, 22171294, and 92056201), the Guangdong Innovative and Entrepreneurial Research Team Program (2016ZT06Y337), the Guangdong Provincial Key Laboratory of Chiral Molecule, and the Natural Science Foundation of Guangdong Province (2021A1515010401) and Drug Discovery (2019B030301005) is greatly acknowledged.

PY - 2023/1/28

Y1 - 2023/1/28

N2 - A Cu(I)-catalyzed three-component reaction of cyclopropenes, enamines and aldehydes has been realized. This reaction proceeds via the interception of carbonyl oxonium ylide intermediates with α, β-unsaturated iminium ions that are in situ generated from enamines and aldehydes under the catalysis of Cu(MeCN)4PF6, leading to the desired γ-butenolide derivatives in good yields and with moderate diastereoselectivities. Access to these derivatives with tethered ketone and alkynal groups will expand the structural diversity of multi-substituted butenolides.

AB - A Cu(I)-catalyzed three-component reaction of cyclopropenes, enamines and aldehydes has been realized. This reaction proceeds via the interception of carbonyl oxonium ylide intermediates with α, β-unsaturated iminium ions that are in situ generated from enamines and aldehydes under the catalysis of Cu(MeCN)4PF6, leading to the desired γ-butenolide derivatives in good yields and with moderate diastereoselectivities. Access to these derivatives with tethered ketone and alkynal groups will expand the structural diversity of multi-substituted butenolides.

UR - https://www.scopus.com/pages/publications/85145837551

U2 - 10.1039/d2ob02075k

DO - 10.1039/d2ob02075k

M3 - Journal article

C2 - 36594521

AN - SCOPUS:85145837551

SN - 1477-0520

VL - 21

SP - 783

EP - 788

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 4

ER -

Copper-catalyzed multicomponent assembly of γ-butenolides via the interception of carbonyl ylides with iminium ions

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