Capitalizing on the propensity of 1,2-amino group migration in γ-aminocyclopentenone with a suitable promoter, gem-diarylequipped systems unfolded an unprecedented avenue for the Lewis acid promoted displacement of γ-aniline group with nucleophiles such as indole. Such transformation, besides providing a means for direct γ- functionalization of cyclopentenones, presented innumerable scope for β,γ-annulation. Various tailored indolo bisnucleophiles were explored in the current study that rendered an array of indole alkaloid-like compounds in excellent yields and selectivity through one-pot operation. Analysis of collective experimental observation along with designed control experiments strongly suggested the possibility of a retro aza- Piancatelli rearrangement, which is hitherto unknown in the context. Such repertoire could find potential applications in the synthesis of complex assemblies from the Piancatelli rearrangement and related processes. © 2022 Georg Thieme Verlag. All rights reserved.