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The efficient silylation of alcohols with di- and trialkynylsilanes was achieved under base-catalyzed conditions to afford alkynyl silyl ethers and symmetrical alkynyl silaketals in good yield. A selective alcoholysis of dialkynyl silyl ethers to mixed silaketals was also demonstrated. These products served as substrates for enyne ring-closing metathesis and, consequently, as precursors to stereochemically defined 1,3-dienes.