Palladium-Catalyzed Synthesis of Spiro[2.4]heptanes: Ligand-Dependent Position Control in the Nucleophilic Attack to a -Allylpalladium Intermediate

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• 作者：Ryo Shintani ; Soyoung Park ; Tamio Hayashi
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：December 5, 2007
• 年：2007
• 卷：129
• 期：48
• 页码：14866 - 14867
• 全文大小：58K
• 年卷期：v.129,no.48(December 5, 2007)
• ISSN：1520-5126

文摘

A palladium-catalyzed intermolecular cycloaddition of -methylidene--valerolactones with electron-deficient olefins has been developed for the synthesis of spiro[2.4]heptanes with high selectivity through a nucleophilic ring closure to the central carbon of a -allylpalladium intermediate. It was found that the course of the reaction is dependent on the ligand employed, and selective [4 + 2] cycloadditions can also be achieved by the use of a bulky monophosphine ligand.