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

研究成果: 雜誌貢獻文章

16 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 2.5 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.

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 七月 27

    指紋

ASJC Scopus subject areas

  • Medicine(all)

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