Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates

Balraj Gopula; Yun Fan Tsai; Ting Shen Kuo; Ping Yu Wu; Julian P. Henschke; Hsyueh Liang Wu

doi:10.1021/acs.orglett.5b00080

Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates

Balraj Gopula, Yun Fan Tsai, Ting Shen Kuo, Ping Yu Wu, Julian P. Henschke^*, Hsyueh Liang Wu

^*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

27 引文斯高帕斯（Scopus）

摘要

The asymmetric conjugate addition of arylboronic acids to substituted and unsubstituted β-pyrazol-1-yl (E)-tert-butyl acrylates 4 catalyzed by 5 mol % of the Rh(I)/diene 2a catalyst provided the corresponding addition products in 44-98% yield and 91->99.5% ee. The method was applied to the formal synthesis of (3S)-3-aryl-3-(pyrazol-1-yl)propanoic acid 1b with agonistic activity toward the human GPR40 G-protein coupled receptor.

原文	英語
頁（從 - 到）	1142-1145
頁數	4
期刊	Organic Letters
卷	17
發行號	5
DOIs	https://doi.org/10.1021/acs.orglett.5b00080
出版狀態	已發佈 - 2015 3月 6

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

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10.1021/acs.orglett.5b00080

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title = "Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates",

abstract = "The asymmetric conjugate addition of arylboronic acids to substituted and unsubstituted β-pyrazol-1-yl (E)-tert-butyl acrylates 4 catalyzed by 5 mol % of the Rh(I)/diene 2a catalyst provided the corresponding addition products in 44-98% yield and 91->99.5% ee. The method was applied to the formal synthesis of (3S)-3-aryl-3-(pyrazol-1-yl)propanoic acid 1b with agonistic activity toward the human GPR40 G-protein coupled receptor.",

author = "Balraj Gopula and Tsai, {Yun Fan} and Kuo, {Ting Shen} and Wu, {Ping Yu} and Henschke, {Julian P.} and Wu, {Hsyueh Liang}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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day = "6",

doi = "10.1021/acs.orglett.5b00080",

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T1 - Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates

AU - Gopula, Balraj

AU - Tsai, Yun Fan

AU - Kuo, Ting Shen

AU - Wu, Ping Yu

AU - Henschke, Julian P.

AU - Wu, Hsyueh Liang

PY - 2015/3/6

Y1 - 2015/3/6

N2 - The asymmetric conjugate addition of arylboronic acids to substituted and unsubstituted β-pyrazol-1-yl (E)-tert-butyl acrylates 4 catalyzed by 5 mol % of the Rh(I)/diene 2a catalyst provided the corresponding addition products in 44-98% yield and 91->99.5% ee. The method was applied to the formal synthesis of (3S)-3-aryl-3-(pyrazol-1-yl)propanoic acid 1b with agonistic activity toward the human GPR40 G-protein coupled receptor.

AB - The asymmetric conjugate addition of arylboronic acids to substituted and unsubstituted β-pyrazol-1-yl (E)-tert-butyl acrylates 4 catalyzed by 5 mol % of the Rh(I)/diene 2a catalyst provided the corresponding addition products in 44-98% yield and 91->99.5% ee. The method was applied to the formal synthesis of (3S)-3-aryl-3-(pyrazol-1-yl)propanoic acid 1b with agonistic activity toward the human GPR40 G-protein coupled receptor.

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DO - 10.1021/acs.orglett.5b00080

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SN - 1523-7060

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SP - 1142

EP - 1145

JO - Organic Letters

JF - Organic Letters

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Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates

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