Cationic Gold(I)-Catalyzed Cascade Bicyclizations for Divergent Synthesis of (Spiro)polyheterocycles

We herein report an expeditious synthetic strategy to access diverse (spiro)polyheterocycles from easily available starting materials in two operational steps including an Ugi four-component reaction and a cationic gold(I)-catalyzed cascade bicyclization. Divergent synthesis of these structurally complex pyrido[2,1-a]isoindol-4(6H)-ones and spiroisoquinoline-pyrrole-3,5′-diones via a cascade nucleophilic cyclization/intramolecular 1,3-migration/1,5-enyne cycloisomerization process and a tandem hydroamination/Michael addition sequence, respectively, was controlled by substituents, where the electronic effect on the migrating groups and steric effect of the secondary amide moieties play crucial roles. © 2018 American Chemical Society.

Authors
Li Z.1 , Song L.1 , Meervelt L.V.2 , Tian G.1 , Van Der Eycken E.V.
Journal
Publisher
American Chemical Society
Number of issue
7
Language
English
Pages
6388-6393
Status
Published
Volume
8
Year
2018
Organizations
  • 1 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Heverlee, Leuven, 3001, Belgium
  • 2 Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Heverlee, Leuven, 3001, Belgium
  • 3 Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
Keywords
1,3-migration; cascade cyclization; gold catalysis; heterocycles; substrate control and divergent synthesis
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/6537/