A chemoselective method for the carbonylation of allylic substrates CH 2 =CHCH 2 X (X = OAc, OC(O)CH 2 CN, OPh, OEt, OC- CN), leading to alkyl succinates with preservation of the X group, under Pd(II)-catalyzed oxidative carbonylation conditions, has been developed. Our method shows a completely different inverse chemoselectivity with respect to the "classical" substitutive carbonylation of the allyl compounds, which is known to provide β,γ-unsaturated carbonyl derivatives through the formation of a π-allylpalladium intermediate. An accurate study, carried out using allyl acetate as model substrate, allowed to maximize the selectivity in the envisioned 2-CH 2 X substituted succinates. The best catalyst is generated in situ by mixing Pd(TFA) 2 (TFA = trifluoroacetate) and the N,N'-di(anthracen-9-yl)butane-2,3-diimine ligand. p-Benzoquinone was used as oxidant in presence of benzyl alcohol, which acts as a nucleophile and as a solvent, under 4 bar of CO at 20 °C. A combined effect of the ligand and the nucleophile, rationalized through DFT calculations, has been observed both in promoting the bis-alkoxycarbonylation process and in preventing π-allylpalladium-mediated side reactions, allowing the attainment of succinate derivatives with moderate to good yields.