Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams: Preparation of Chiral 4-Aryl-2-Pyrrolidones

Jo Hsuan Fang, Chiung An Chang, Balraj Gopula, Ting Shen Kuo, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The preparation of chiral 4-aryl-2-pyrrolidones by conjugate addition catalyzed by a rhodium(I) complex, comprising the chiral bicyclo[2.2.1] diene ligand 1e, is reported. The reaction of various arylboronic acids and α,β-unsaturated γ-lactams 2 bearing various N-substituents proceeds in a highly stereoselective fashion (93-99.5% ee) even in the presence of only 0.5mol% of the Rh catalyst affording the corresponding addition products in 31-99% yield.

Original languageEnglish
Pages (from-to)481-485
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume5
Issue number4
DOIs
Publication statusPublished - 2016 Apr 1

Fingerprint

Bearings (structural)
Lactams
Rhodium
Ligands
Catalysts
Acids
2-pyrrolidone

Keywords

  • 4-aryl-2-pyrrolidones
  • Arylboronic acids
  • Conjugate addition
  • Homogeneous catalysis
  • Rhodium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams : Preparation of Chiral 4-Aryl-2-Pyrrolidones. / Fang, Jo Hsuan; Chang, Chiung An; Gopula, Balraj; Kuo, Ting Shen; Wu, Ping Yu; Henschke, Julian P.; Wu, Hsyueh Liang.

In: Asian Journal of Organic Chemistry, Vol. 5, No. 4, 01.04.2016, p. 481-485.

Research output: Contribution to journalArticle

Fang, Jo Hsuan ; Chang, Chiung An ; Gopula, Balraj ; Kuo, Ting Shen ; Wu, Ping Yu ; Henschke, Julian P. ; Wu, Hsyueh Liang. / Rhodium-Catalyzed Enantioselective Arylation of N-Substituted α,β-Unsaturated γ-Lactams : Preparation of Chiral 4-Aryl-2-Pyrrolidones. In: Asian Journal of Organic Chemistry. 2016 ; Vol. 5, No. 4. pp. 481-485.
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