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Catalytic Dehydrative Lactonization of Allylic Alcohols
A convenient strategy for the synthesis
of phthalides and γ-butyrolactones
is reported. The method utilizes readily prepared allylic alcohols
in formal AuÂ(I)- and PdÂ(II)-catalyzed S<sub>N</sub>2′ reactions.
Using these catalysts, exclusive formation of the desired five-membered
lactones is observed, completely avoiding the competing direct lactonization
pathway that forms the undesired seven-membered ring with protic acids
and alternative metal salts. This mild and operationally simple method
notably tolerates exomethylene groups and should find use in both
phthalide and terpene syntheses