Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures
Chenna Jagadeesh, Biplab Mondal, Sourav Pramanik, Dinabandhu Das, Jaideep Saha
Abstract
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.
Topics & Concepts
CyclopentenoneIndole testChemistryEnoneRing (chemistry)Reactivity (psychology)StereochemistryCombinatorial chemistrySelectivityOrganic chemistryCatalysisAlternative medicineMedicinePathologySynthesis of Indole DerivativesAsymmetric Synthesis and CatalysisMarine Sponges and Natural Products