Rhodium-Catalyzed Intramolecular [5+2] Cycloaddition of Inverted 3-Acyloxy-1,4-enyne and Alkyne: Experimental and Theoretical Studies

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• 作者：Dr. Xiaoxun Li ; Wangze Song ; Xiaona Ke ; Prof. Dr. Xiufang Xu ; Prof. Dr. Peng Liu ; Prof. Dr. K. N. Houk ; Dr. Xian-liang Zhao and Prof. Dr. Weiping Tang
• 刊名：Chemistry - A European Journal
• 出版年：2016
• 出版时间：May 17, 2016
• 年：2016
• 卷：22
• 期：21
• 页码：7079-7083
• 全文大小：451K
• ISSN：1521-3765

文摘

By switching the position of the alkene and alkyne, a new type of 3-acyloxy-1,4-enyne (ACE) five-carbon building block was developed for Rh-catalyzed intramolecular [5+2] cycloaddition. An electron-withdrawing acyl group on the alkyne termini of the ACE was essential for a regioselective 1,2-acyloxy migration. This new method provided bicyclic [5.3.0]decatrienes that are different from previous methods because of the positions of the alkenes and the acyloxy group. Multiple mechanistic pathways become possible for this new [5+2] cycloaddition and they are investigated by computational studies.