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Construction of Hydrodibenzo[b,d]furan Frameworks from Morita-Baylis-Hillman Carbonates of Isatins and o-Hydroxy Enones via Palladium and Brønsted Base Relay Catalysis.

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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… Click to show full 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.

Keywords: hillman carbonates; relay catalysis; morita baylis; baylis hillman

Journal Title: Organic letters
Year Published: 2021

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