Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides | |
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學年 | 103 |
學期 | 2 |
出版(發表)日期 | 2015-07-27 |
作品名稱 | Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides |
作品名稱(其他語言) | |
著者 | 謝仁傑 |
單位 | |
出版者 | |
著錄名稱、卷期、頁數 | Chemistry 21 (31), p.11050–11055 |
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. |
關鍵字 | chiral ligands;conjugate addition;enantioselectivity;pyrrolidine;rhodium |
語言 | en |
ISSN | 0972-8376 |
期刊性質 | 國外 |
收錄於 | SCI |
產學合作 | |
通訊作者 | 謝仁傑 |
審稿制度 | 是 |
國別 | DEU |
公開徵稿 | |
出版型式 | ,電子版,紙本 |
相關連結 |
機構典藏連結 ( http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/103481 ) |