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Issue 11, 2016
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Diastereoselective synthesis of 2,5-disubstituted-3-hydroxy-tetrahydrofurans through a counterion-directed Tsuji–Trost reaction

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Abstract

Tsuji–Trost Counterion Directed Catalysis (CDC) allows the diastereoselective synthesis of 5-alkyl-3-hydroxy-2-vinyl tetrahydrofurans in high yields using easily accessible 4,6-dihydroxyalk-2-en-1-yl esters as substrates. The mechanism of this reaction has been investigated by relying on DFT predictions and experimental confirmations based on deuterium labeling and modification of the pKa of counterions which demonstrates that the favored transition state is tightly organized through the formation of a network of H-bonds.

Graphical abstract: Diastereoselective synthesis of 2,5-disubstituted-3-hydroxy-tetrahydrofurans through a counterion-directed Tsuji–Trost reaction

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Publication details

The article was received on 08 Jul 2016, accepted on 02 Sep 2016 and first published on 02 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00337K
Citation: Org. Chem. Front., 2016,3, 1462-1466
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    Diastereoselective synthesis of 2,5-disubstituted-3-hydroxy-tetrahydrofurans through a counterion-directed Tsuji–Trost reaction

    X. Caumes, L. Jeanne-Julien, C. Khelifi, V. Gandon and E. Roulland, Org. Chem. Front., 2016, 3, 1462
    DOI: 10.1039/C6QO00337K

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