Metal-Catalyzed [6 + 3] Cycloaddition of Tropone with Azomethine Ylides: A Practical Access to Piperidine-Fused Bicyclic Heterocycles

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• 作者：Honglei Liu ; Yang Wu ; Yan Zhao ; Zhen Li ; Lei Zhang ; Wenjun Yang ; Hui Jiang ; Chengfeng Jing ; Hao Yu ; Bo Wang ; Yumei Xiao ; Hongchao Guo
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：February 12, 2014
• 年：2014
• 卷：136
• 期：6
• 页码：2625-2629
• 全文大小：294K
• ISSN：1520-5126

文摘

The first metal-catalyzed [6 + 3] cycloaddition of tropone with azomethine ylides has been developed. With the use of a chiral ferrocenylphosphine鈥揷opper(I) complex as the catalyst, the asymmetric variant of the [6 + 3] cycloaddition has also been successfully achieved. The reactions proceeded smoothly under mild conditions, affording piperidine-fused bicyclic heterocycles in moderate to high yields with good to excellent diastereo- and enantioselectivies. The procedures are operationally simple and the catalysts are cheap and readily accessible, thus providing a practical approach to piperidine-fused bicyclic heterocycles.