Abstract
The silver-catalyzed rearrangement of propargyl alcohols yields α,β-unsaturated ketones in good yield with moderate diastereoselectivity in some cases. The reaction is mediated by carbon dioxide and is proposed to proceed through a Meyer-Schuster reaction pathway. The solvent plays an important role in controlling the reaction pathway. The use of formamide gave the best results, proceeding through the [3,3]-sigmatropic pathway, whereas toluene gave the cyclic carbonates.
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