Rh(III)-Catalyzed Diastereoselective Annulation of Amides with Quinone Monoacetals: Access to Bridged Nine-Membered Heterocycles via C–H Activation

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• 作者：Wei Yang ; Jinhuan Dong ; Jingyi Wang ; Xianxiu Xu
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：616-619
• 全文大小：417K
• ISSN：1523-7052

文摘

An unprecedented Rh(III)-catalyzed annulation of various benzamides and acrylamides with quinone monoacetals was developed for the facile and efficient one-pot synthesis of bridged nine-membered benzo[c]azonine-1,5(2H)-diones and 2-azabicyclo[4.3.1]dec-4-ene-3,8-diones. It is the first example of synthesis of nine-membered heterocycles through Rh(III)-catalyzed C–H bond functionalization, and both aryl and vinyl C–H bonds are tolerant in this reaction. A plausible mechanism is proposed on the basis of control experiments.