Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights

详细信息    查看全文

• 作者：Yang Zheng ; Yongjian Chi ; Ming Bao ; Lihua Qiu ; Xinfang Xu
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 17, 2017
• 年：2017
• 卷：82
• 期：4
• 页码：2129-2135
• 全文大小：447K
• ISSN：1520-6904

文摘

A general and unprecedented gold-catalyzed tandem dual heterocyclization reaction of enynones with 1,3,5-triazines has been developed, which provides bicyclic fused furans in high to excellent yields under mild reaction conditions. In addition, mechanistic studies indicate that the reaction goes through a stepwise [3+2+2]-cycloaddition of furanyl gold intermediate, which is generated from gold-catalyzed cyclization of enynone, with two molecules of formaldimines derived in situ from 1,3,5-triazine, instead of formal [4+3]-cycloaddition.