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 journalArticle

14 Citations (Scopus)

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 languageEnglish
Pages (from-to)1142-1145
Number of pages4
JournalOrganic Letters
Volume17
Issue number5
DOIs
Publication statusPublished - 2015 Mar 6

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Acrylates
Rhodium
dienes
acrylates
G-Protein-Coupled Receptors
rhodium
acids
Catalysts
Acids
proteins
catalysts
synthesis
products
propionic acid
tert-butyl acrylate
human FFAR1 protein

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates. / Gopula, Balraj; Tsai, Yun Fan; Kuo, Ting Shen; Wu, Ping Yu; Henschke, Julian P.; Wu, Hsyueh Liang.

In: Organic Letters, Vol. 17, No. 5, 06.03.2015, p. 1142-1145.

Research output: Contribution to journalArticle

Gopula, Balraj ; Tsai, Yun Fan ; Kuo, Ting Shen ; Wu, Ping Yu ; Henschke, Julian P. ; Wu, Hsyueh Liang. / Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates. In: Organic Letters. 2015 ; Vol. 17, No. 5. pp. 1142-1145.
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