Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins: Formal synthesis of (S)-SKF 38393

Kung Chih Huang, Balraj Gopula, Ting Shen Kuo, Chien Wei Chiang, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

An efficient enantioselective addition of an array of arylboronic acids to various β-nitrostyrenes catalyzed by a novel and reactive rhodium-diene catalyst (S/C up to 1000) was developed, providing β,β- diarylnitroethanes in good to high yields (62-99%) with excellent enantioselectivities (85-97% ee). The method was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly providing the desired products with high enantioselectivities and yields. The usefulness of this method was demonstrated in the formal synthesis of the enantiomer of the dopamine receptor agonist and antagonist, SKF 38393.

Original languageEnglish
Pages (from-to)5730-5733
Number of pages4
JournalOrganic Letters
Volume15
Issue number22
DOIs
Publication statusPublished - 2013 Nov 15

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2,3,4,5-Tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine
Rhodium
Enantioselectivity
rhodium
dopamine
acids
Acids
Dopamine Antagonists
Enantiomers
enantiomers
Dopamine Agonists
dienes
synthesis
catalysts
Catalysts
products

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins : Formal synthesis of (S)-SKF 38393. / Huang, Kung Chih; Gopula, Balraj; Kuo, Ting Shen; Chiang, Chien Wei; Wu, Ping Yu; Henschke, Julian P.; Wu, Hsyueh Liang.

In: Organic Letters, Vol. 15, No. 22, 15.11.2013, p. 5730-5733.

Research output: Contribution to journalArticle

Huang, Kung Chih ; Gopula, Balraj ; Kuo, Ting Shen ; Chiang, Chien Wei ; Wu, Ping Yu ; Henschke, Julian P. ; Wu, Hsyueh Liang. / Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins : Formal synthesis of (S)-SKF 38393. In: Organic Letters. 2013 ; Vol. 15, No. 22. pp. 5730-5733.
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