2-(tert-Butyldimethylsilyl)-3-furoic acid 7 was regiospecifically lithiated at the C-4 position when treated with 2.5 equiv. of butyllithium (at –20 °C) in either tetrahydrofuran or 1,2-dimethoxyethane; trapping of the dianion with a variety of electrophiles provided 2,3,4-trisubstituted furans in good to excellent yield.
S. Yu and B. A. Keay, J. Chem. Soc., Perkin Trans. 1, 1991, 2600 DOI: 10.1039/P19910002600
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