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

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

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.

Original language	English
Pages (from-to)	1142-1145
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.5b00080
State	Published - 6 Mar 2015
Externally published	Yes

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@article{4a20419ed2cb4803a7183bea09899d45,

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",

month = mar,

day = "6",

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

language = "English",

volume = "17",

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journal = "Organic Letters",

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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.

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

U2 - 10.1021/acs.orglett.5b00080

DO - 10.1021/acs.orglett.5b00080

M3 - Article

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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