High and opposite enantiodiscriminations were observed between tertiary amides and secondaryamides in the sparteine-mediated lateral metalation−allylation of 2-ethyl-m-toluamide derivatives(2a, 2e). The results described above have been applied for the formal synthesis of both enantiomersof curcuphenol. The brief mechanistic studies suggested that stereoinformation was introducedafter the deprotonation step.