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Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media

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Abstract

3-Arylmethylidenetetrahydrofuran-2,4-diones were smoothly reduced to the corresponding 3-benzyl derivatives in 50–98% yield with triethylsilane in trifluoroacetic acid or with sodium cyanotrihydridoborate in the system tetrahydrofuran-2 N hydrochloric acid. The reduction of 3-(3-arylprop-2-en-1-ylidene)-tetrahydrofuran-2,4-diones with sodium cyanotrihydridoborate gave 3-cinnamyltetrahydrofuran-2,4-diones as the only products.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, Minsk, 220141, Belarus

    F. S. Pashkovskii, E. M. Shchukina & F. A. Lakhvich

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  1. F. S. Pashkovskii
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  2. E. M. Shchukina
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  3. F. A. Lakhvich
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Correspondence to F. S. Pashkovskii.

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Original Russian Text © F.S. Pashkovskii, E.M. Shchukina, F.A. Lakhvich, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 6, pp. 871–875.

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Pashkovskii, F.S., Shchukina, E.M. & Lakhvich, F.A. Chemoselective reduction of 3-arylmethylidenetetrahydrofuran-2,4-diones with triethylsilane and sodium cyanotrihydridoborate in acid media. Russ J Org Chem 45, 858–862 (2009). https://doi.org/10.1134/S1070428009060098

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  • DOI: https://doi.org/10.1134/S1070428009060098

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