Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation

Yan Cheng Liou; Yin Hsiang Su; Kuan Chun Ku; Athukuri Edukondalu; Chun Kai Lin; You Syuan Ke; Praneeth Karanam; Chia Jui Lee; Wenwei Lin

doi:10.1021/acs.orglett.9b03116

Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation

Yan Cheng Liou
, Yin Hsiang Su
, Kuan Chun Ku
, Athukuri Edukondalu
, Chun Kai Lin
, You Syuan Ke
, Praneeth Karanam
, Chia Jui Lee
, Wenwei Lin^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

17 引文斯高帕斯（Scopus）

摘要

We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.

原文	英語
頁（從 - 到）	8339-8343
頁數	5
期刊	Organic Letters
卷	21
發行號	20
DOIs	https://doi.org/10.1021/acs.orglett.9b03116
出版狀態	已發佈 - 2019 10月 18

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

存取文件

10.1021/acs.orglett.9b03116

其它文件與鏈接

CCDC 1484673: Experimental Crystal Structure Determination
Liou, Y.-C. (Contributor), Su, Y.-H. (Contributor), Ku, K.-C. (Contributor), Edukondalu, A. (Contributor), Lin, C.-K. (Contributor), Ke, Y.-S. (Contributor), Karanam, P. (Contributor), Lee, C.-J. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1ltxp0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1ltxp0&sid=DataCite
資料集: Dataset
CCDC 1561010: Experimental Crystal Structure Determination
Liou, Y.-C. (Contributor), Su, Y.-H. (Contributor), Ku, K.-C. (Contributor), Edukondalu, A. (Contributor), Lin, C.-K. (Contributor), Ke, Y.-S. (Contributor), Karanam, P. (Contributor), Lee, C.-J. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1pdc5m, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1pdc5m&sid=DataCite
資料集: Dataset
CCDC 1947032: Experimental Crystal Structure Determination
Liou, Y.-C. (Contributor), Su, Y.-H. (Contributor), Ku, K.-C. (Contributor), Edukondalu, A. (Contributor), Lin, C.-K. (Contributor), Ke, Y.-S. (Contributor), Karanam, P. (Contributor), Lee, C.-J. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc23c1h1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23c1h1&sid=DataCite
資料集: Dataset

引用此

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title = "Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation",

abstract = "We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.",

author = "Liou, \{Yan Cheng\} and Su, \{Yin Hsiang\} and Ku, \{Kuan Chun\} and Athukuri Edukondalu and Lin, \{Chun Kai\} and Ke, \{You Syuan\} and Praneeth Karanam and Lee, \{Chia Jui\} and Wenwei Lin",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

day = "18",

doi = "10.1021/acs.orglett.9b03116",

language = "English",

volume = "21",

pages = "8339--8343",

journal = "Organic Letters",

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publisher = "American Chemical Society",

number = "20",

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TY - JOUR

T1 - Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation

AU - Liou, Yan Cheng

AU - Su, Yin Hsiang

AU - Ku, Kuan Chun

AU - Edukondalu, Athukuri

AU - Lin, Chun Kai

AU - Ke, You Syuan

AU - Karanam, Praneeth

AU - Lee, Chia Jui

AU - Lin, Wenwei

PY - 2019/10/18

Y1 - 2019/10/18

N2 - We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.

AB - We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.

UR - https://www.scopus.com/pages/publications/85073108596

UR - https://www.scopus.com/pages/publications/85073108596#tab=citedBy

U2 - 10.1021/acs.orglett.9b03116

DO - 10.1021/acs.orglett.9b03116

M3 - Article

C2 - 31566385

AN - SCOPUS:85073108596

SN - 1523-7060

VL - 21

SP - 8339

EP - 8343

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1484673: Experimental Crystal Structure Determination

CCDC 1561010: Experimental Crystal Structure Determination

CCDC 1947032: Experimental Crystal Structure Determination

引用此