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Palladium-catalyzed synthesis of 4-oxaspiro[2.4]heptanes via central attack of oxygen nucleophiles to π-allylpalladium intermediates.

Organic letters (2012-04-26)
Ryo Shintani, Tomoaki Ito, Tamio Hayashi
ABSTRACT

A palladium-catalyzed decarboxylative cyclopropanation of γ-methylidene-δ-valerolactones with aromatic aldehydes has been developed to give 4-oxaspiro[2.4]heptanes with high selectivity. The site of nucleophilic attack to a π-allylpalladium intermediate has been controlled with a sterically demanding phosphine ligand. The course of the reaction is highly dependent on ligands and solvents, and selective formation of methylenetetrahydropyrans has also been realized.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
δ-Valerolactone, technical grade