Construction of Hydrodibenzo[<i>b</i>,<i>d</i>]furan Frameworks from Morita–Baylis–Hillman Carbonates of Isatins and <i>o</i>-Hydroxy Enones via Palladium and Brønsted Base Relay Catalysis
Ze-Liang He, Peng Chen, Zhichao Chen, Wei Du, Ying‐Chun Chen
Abstract
A cascade assembly between isatin-derived Morita–Baylis–Hillman carbonates and o-hydroxybenzylideneacetones has been developed under the relay catalysis of Pd(PPh3)4 and DBU, affording a spectrum of 1,2,3,4-tetrahydrodibenzo[b,d]furan architectures incorporating a spirooxindole motif in moderate to good yields with excellent diastereoselectivity. The fused indole analogues were similarly furnished by employing the benzylideneacetones having an o-TsNH group.
Topics & Concepts
ChemistryIsatinFuranCatalysisIndole testPalladiumStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistrySynthesis of Indole DerivativesSynthesis of heterocyclic compoundsSynthesis and Biological Activity