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Issue 11, 2019
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Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

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Abstract

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ethers based on the use of vinylbenziodoxolone (VBX) reagents. The stable VBX reagents were synthesized by stereoselective addition of N- or O-nucleophiles on the corresponding alkynyl reagents in the presence of a catalytic amount of cesium carbonate. The VBX reagents were used in palladium-catalyzed cross-couplings at room temperature to access Z-enamides and enol ethers.

Graphical abstract: Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

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Publication details

The article was received on 13 Dec 2018, accepted on 03 Feb 2019 and first published on 04 Feb 2019


Article type: Edge Article
DOI: 10.1039/C8SC05573D
Citation: Chem. Sci., 2019,10, 3223-3230
  • Open access: Creative Commons BY license
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    Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

    P. Caramenti, N. Declas, R. Tessier, M. D. Wodrich and J. Waser, Chem. Sci., 2019, 10, 3223
    DOI: 10.1039/C8SC05573D

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