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Title: Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures.
Authors: Jagadeesh, Chenna; Mondal, Biplab; Pramanik, Sourav; Das, Dinabandhu; Saha, Jaideep
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.
Subjects: CYCLOPENTENONE; INDOLE compounds; INDOLE; LEWIS acids; INDOLE derivatives; INDOLE alkaloids
Publication: Angewandte Chemie, 2021, Vol 133, Issue 16, p8890
ISSN: 0044-8249
Publication type: Academic Journal
DOI: 10.1002/ange.202016015

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