Reaction Pathways through a [1,5]-Hydride Shift Triggered by Acids: Approach to Bridged-Ring Heterocycles and Polycycles

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• 作者：Le Zhen ; Liang Dai ; Sheng-Qi Yu ; Chao Lin ; Hongbin Sun and Qing-Long Xu
• 刊名：European Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 18, 2017
• 年：2017
• 卷：2017
• 期：3
• 页码：560-569
• 全文大小：1430K
• ISSN：1099-0690

文摘

The [1,5]-hydride shift/cyclization process as a new C_sp³–H bond functionalization has made tremendous advances over the past decades. Herein, we describe reaction pathways for a [1,5]-hydride shift that is triggered by acid. In these transformations, the diene isoindoles are generated in situ and undergo a reaction with different dienophiles to provide access to a series of bridged-ring heterocycles and polycycles in good yields (up to 94 %). In addition, we found that the choice of acid played a critical role and could be used to control the structure of the final product.