A stereochemical substrate probe was used to assess the factors that affect the stereochemical course of nucleopalladation in the context of an enantioselective Wacker-type reaction. The enantioselectivity correlates directly with the nucleopalladation pathway, and both the neutral-donor and anionic ligands on palladium are capable of controlling selectivity for cis- or trans-nucleopalladation (see scheme; TFA=trifluoroacetate).
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