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

FS Pashkovskii, EM Shchukina, FA Lakhvich

Index: Pashkovskii; Shchukina; Lakhvich Russian Journal of Organic Chemistry, 2009 , vol. 45, # 6 p. 858 - 862

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Abstract

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.