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

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

27 引文 斯高帕斯(Scopus)

摘要

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 2.5mol % of RhI/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. The road to rhodium! Enantioselective conjugate addition of a range of arylboronic acids to variously N-substituted maleimides, catalyzed by RhI complexes prepared in situ using chiral bicyclo[2.2.1]diene ligands, afforded the corresponding 3-arylsuccinimides with up to 98 %ee at 50 C (see scheme).

原文英語
頁(從 - 到)11050-11055
頁數6
期刊Chemistry - A European Journal
21
發行號31
DOIs
出版狀態已發佈 - 2015 7月 27

ASJC Scopus subject areas

  • 催化
  • 有機化學

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