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Issue 49, 2019
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Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction

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Abstract

Bicyclic ether scaffolds are found in a variety of natural products and are of interest in probe and drug discovery. A palladium-catalyzed cascade reaction has been developed to provide efficient access to these scaffolds from readily available linear diene–diol substrates. A Pd redox-relay process is used strategically to transmit reactivity between an initial oxypalladative cyclization and a subsequent π-allyl-Pd cyclization at remote sites. The reaction affords a variety of bicyclic ether scaffolds with complete diastereoselectivity for cis-ring fusion.

Graphical abstract: Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction

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Publication details

The article was received on 16 May 2019, accepted on 17 May 2019 and first published on 31 May 2019


Article type: Communication
DOI: 10.1039/C9CC03775F
Chem. Commun., 2019,55, 7013-7016

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    Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction

    M. C. Lux, M. L. Boby, J. L. Brooks and D. S. Tan, Chem. Commun., 2019, 55, 7013
    DOI: 10.1039/C9CC03775F

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