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Unprecedented Reactivity of γ-Amino Cyclopentenone Enables Diversity-Oriented Access to Functionalized Indoles and Indole-Annulated Ring Structures.

Observation of an unexpected, Lewis acid promoted displacement of latent reactive γ-amino group on cyclopentenone presented unparalleled opportunity for enone functionalization and annulations with indole derivatives, which is developed in the current study. Herein, a vast range of C3/ N -indolyl enones and indole alkaloid-like compound were accessed in excellent yields (up to 99%) and selectivity through a one-pot operation. The mechanism most likely involves an unprecedented trait of Piancatelli-type rearrangement where influence of the gem -diaryl group appeared crucial.