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Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non‐racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π‐acid catalysis. More specifically, a catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel Pd^II‐catalyst containing the imidazole‐basedP,N‐ligand (S)‐StackPhos is reported. The high‐yielding reactions are operationally simple to perform with enantioselectivities up to 99 %ee. This strategy facilitates the replacement of a poor leaving group with what would ostensibly be a better leaving group in the product avoiding complications arising from racemization by equilibration.

Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non‐racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π‐acid catalysis. More specifically, a catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel Pd^II‐catalyst containing the imidazole‐basedP,N‐ligand (S)‐StackPhos is reported. The high‐yielding reactions are operationally simple to perform with enantioselectivities up to 99 %ee. This strategy facilitates the replacement of a poor leaving group with what would ostensibly be a better leaving group in the product avoiding complications arising from racemization by equilibration.