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A Gold‐Catalyzed Domino Cyclization Enabling Rapid Construction of Diverse Polyheterocyclic Frameworks
Author(s) -
He Yi,
Li Zhenghua,
Robeyns Koen,
Van Meervelt Luc,
Van der Eycken Erik V.
Publication year - 2018
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.201710592
Subject(s) - domino , thiophene , furan , combinatorial chemistry , pyrrole , chemistry , indole test , pyrazole , catalysis , sequence (biology) , cascade reaction , stereochemistry , organic chemistry , biochemistry
We report herein an efficient gold(I)‐catalyzed post‐Ugi domino dearomatization/ ipso ‐cyclization/Michael sequence that enables access to libraries of diverse (hetero)arene‐annulated tricyclic heterocycles. This process affords novel complex polycyclic scaffolds in moderate to good yields from readily available acyclic precursors with excellent chemo‐, regio‐, and diastereoselectivity. The power of this strategy has been demonstrated by the rapid synthesis of 40 highly functionalized polyheterocycles bearing indole, pyrrole, (benzo)furan, (benzo)thiophene, pyrazole, and electron‐rich arene groups in two operational steps.