Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions via a conceptually new and stereoselective protocol under Pd catalysis. The in situ formed (Z)‐configured alfa‐amino acid cyclizes to afford an alfa,beta‐unsaturated gamma‐lactam releasing water as the only by‐product. This practical catalytic transformation highlights the use of a carboxyl group acting as a hydrogen donor, stereodirecting and functional group to provide a wide series of pharma‐relevant building blocks. Various control reactions support the crucial role of a carboxyl group in the substrate to mediate these transformations.