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

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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

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Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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