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Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures
Author(s) -
Jagadeesh Chenna,
Mondal Biplab,
Pramanik Sourav,
Das Dinabandhu,
Saha Jaideep
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016015
Subject(s) - cyclopentenone , indole test , chemistry , enone , stereochemistry , ring (chemistry) , selectivity , reactivity (psychology) , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.