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

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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
Volume21
Issue number31
DOIs
Publication statusPublished - 2015 Jul 27

Keywords

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

ASJC Scopus subject areas

  • Medicine(all)

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