Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides
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
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 )

機構典藏連結