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 › 通訊期刊論文 › 同行評審

29 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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@article{68f0d1fdf05b4582bf6a9cbc98de3151,

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{\textendash}98\% yield and 91{\textendash}>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: Copyright {\textcopyright} 2015 American Chemical Society",

year = "2015",

month = mar,

day = "6",

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

language = "English",

volume = "17",

pages = "1142--1145",

journal = "Organic Letters",

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TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/84924234318

UR - https://www.scopus.com/pages/publications/84924234318#tab=citedBy

U2 - 10.1021/acs.orglett.5b00080

DO - 10.1021/acs.orglett.5b00080

M3 - Letter

C2 - 25679334

AN - SCOPUS:84924234318

SN - 1523-7060

VL - 17

SP - 1142

EP - 1145

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Rhodium/Chiral Diene Complexes in the Catalytic Asymmetric Arylation of β-Pyrazol-1-yl Acrylates

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