Direct synthesis of chiral 3-arylsuccinimides by rhodium-catalyzed enantioselective conjugate addition of arylboronic acids to maleimides

Balraj Gopula, Shu Han Yang, Ting Shen Kuo, Jen Chieh Hsieh, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

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Chiral rhodium catalysts comprising 2,5-diaryl- substituted bicyclo[2.2.1]diene ligands L1-L10 were utilized in the enantioselective 1,4-addition reaction of arylboronic acids to N-substituted maleimides. In the presence of 2.5 mol % of Rh(I) /L2, enantioenriched conjugate addition adducts were isolated in 72-99 % yields with 86-98 % ee. This protocol offers a convenient method to access a variety of 3-arylsuccinimides in a highly enantioselective manner. Maleimides with readily cleavable N-protecting groups were tolerated enabling the synthesis of useful synthetic intermediates. Pyrrolidine 4, a biologically active compound, and pyrrolidine 5, an ent-precursor to an HSD-1 inhibitor, were synthesized to demonstrate the utility of this method.

Original languageEnglish
Pages (from-to)11050-11055
Number of pages6
JournalChemistry - A European Journal
Issue number31
Publication statusPublished - 2015 Jul 27



  • chiral ligands
  • conjugate addition
  • enantioselectivity
  • pyrrolidine
  • rhodium

ASJC Scopus subject areas

  • Medicine(all)

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