1,3-Dipolar cycloaddition reaction for diastereoselective synthesis of functionalized dihydrospiro[indoline-3,2′-pyrroles]

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• 作者：Ping Wu^a ; Hong Gao^b ; Jing Sun^b ; Chao-Guo Yan^b ; ^{cgyan@yzu.edu.cn}
• 关键词：One-pot reaction ; 1 ; 3-Dipolar cycloaddition ; Azomethine ylide ; Electron-deficient alkyne ; Spiro[indoline-3 ; 2&prime ; -pyrrole]
• 刊名：Chinese Chemical Letters
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：28
• 期：2
• 页码：329-332
• 全文大小：405 K
• 卷排序：28

文摘

The BF3OEt2 catalyzed one-pot 1,3-dipolar cycloaddition reaction of benzylamines, isatins and dimethyl acetylenedicarboxylate in dry methylene dichloride afforded the functionalized dihydrospiro[indoline-3,2′-pyrroles] in moderate to good yields and with high diastereoselectivity. The reaction was accomplished by the tandem 1,3-dioplar cycloaddition of in situ generated azomethine ylide with acetylenedicarboxylate and the nucleophilic addition of pyrrole ring to second molecular acetylenedicarboxylate.