Journal
ACS CATALYSIS
Volume 8, Issue 7, Pages 6388-6393Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b01789
Keywords
gold catalysis; heterocycles; cascade cyclization; 1,3-migration; substrate control and divergent synthesis
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Funding
- F.W.O. [Fund for Scientific Research Flanders (Belgium)]
- Research Fund of the University of Leuven (KU Leuven)
- RUDN University Program 5-100
- China Scholarship Council (CSC)
- Hercules Foundation [AKUL/09/0035]
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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]isoindo1-4(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.
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