The palladium(0)‐catalyzed alkylation of 2,3‐bis(acetoxymethyl)bicyclo[2.2.1]hepta‐2,5‐diene 1 with malonate‐type enolates as nucleophiles is investigated. A monoalkylated product is formed first, and undergoes (depending on the nucleophile used) a second intramolecular reaction leading to spirocyclopropane‐annulated bicyclo[2.2.1]heptene derivatives 5. The formation of endo spirobicyclic cyclopropanes adducts as major isomer is rationalized by assuming formation of an intermediate exo‐(π‐allyl)palladium complex.
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