Abstract
β-Keto esters derived from 2-(trimethylsilyl)ethanol undergo cleavage and decarboxylation when treated with 0.75 equivalents of tetrabutylammonium fluoride trihydrate in tetrahydrofuran at 50 ˚C, while β-keto esters derived from methanol, tert-butyl alcohol, allyl alcohol, or benzyl alcohol stay intact. Conversely, methyl-, tert-butyl-, allyl-, or benzyl β-keto esters can be cleaved and decarboxylated without the 2-(trimethylsilyl)ethyl β-keto esters being affected. Similarly, mixed bis(β-keto esters) derived from 2-(trimethylsilyl)ethanol and methanol, tert-butyl alcohol, allyl alcohol, or benzyl alcohol can be defunctionalized chemoselectively under the same reaction conditions.
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