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

R Shintani, S Park, T Hayashi

Index: Shintani, Ryo; Murakami, Masataka; Hayashi, Tamio Journal of the American Chemical Society, 2007 , vol. 129, # 41 p. 12356 - 12357

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Citation Number: 45

Abstract

A palladium-catalyzed intermolecular cycloaddition of γ-methylidene-δ-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 π-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 ...