Efficient synthesis of alkynylsilyl ethers and silaketals via base-induced alkynylsilane alcoholysis.
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.
Grimm
Jonathan B
JB
Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
Lee
Daesung
D
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D000468:Alkalies / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*
D000438:Alcohols; D000468:Alkalies; D004987:Ethers; D009942:Organometallic Compounds; D012821:Silanes