Palladium-Catalyzed Intermolecular Oxyvinylcyclization of Alkenes with Alkynes: An Approach to 3-Methylene 纬-Lactones and Tetrahydrofurans

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• 作者：Zhenming Zhang ; Lu Ouyang ; Wanqing Wu ; Jianxiao Li ; Zhicai Zhang ; Huanfeng Jiang
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：November 21, 2014
• 年：2014
• 卷：79
• 期：22
• 页码：10734-10742
• 全文大小：414K
• ISSN：1520-6904

文摘

A novel chloropalladation-initiated intermolecular oxyvinylcyclization of alkenes with alkynoic acids or alkynols is developed. This protocol provides a series of 3-methylene 纬-lactone and tetrahydrofuran derivatives in moderate to excellent yields with high stereoselectivities in the presence of PdCl₂ and CuCl₂ or CuCl₂路2H₂O. Besides a broad substrate scope, this method has the advantages of mild reaction conditions and easily accessible starting materials. Furthermore, the construction of C鈥揅l, C(sp²)鈥揅(sp³), and C鈥揙 bonds in one step was also achieved in this transformation.