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

化學系

研究成果: 雜誌貢獻 › 文章 › 同行評審

4 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 十月 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b03116

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Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation. / Liou, Yan Cheng; Su, Yin Hsiang; Ku, Kuan Chun; Edukondalu, Athukuri; Lin, Chun Kai; Ke, You Syuan; Karanam, Praneeth; Lee, Chia Jui; Lin, Wenwei.

於: Organic Letters, 卷 21, 編號 20, 18.10.2019, p. 8339-8343.

研究成果: 雜誌貢獻 › 文章 › 同行評審

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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 = "Funding Information: We thank the Ministry of Science and Technology of the Republic of China (MOST 107-2628-M-003-001-MY3) for financial support.",

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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

N1 - Funding Information: We thank the Ministry of Science and Technology of the Republic of China (MOST 107-2628-M-003-001-MY3) for financial support.

PY - 2019/10/18

Y1 - 2019/10/18

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