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    題名: Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides
    作者: 謝仁傑
    關鍵詞: chiral ligands;conjugate addition;enantioselectivity;pyrrolidine;rhodium
    日期: 2015-07-27
    上傳時間: 2015-07-28 16:34:56 (UTC+8)
    出版者: Trade Science, Inc.
    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.
    關聯: Chemistry 21 (31), p.11050–11055
    DOI: 10.1002/chem.201501059
    顯示於類別:[化學學系暨研究所] 期刊論文

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