In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers.
Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes(2)Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.
Kerr
William J
WJ
Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland, UK G1 1XL. w.kerr@strath.ac.uk
Watson
Allan J B
AJ
Hayes
Douglas
D
D002244:Carbon / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D017616:Magnesium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D004987:Ethers; D007659:Ketones; D017616:Magnesium Compounds; D012821:Silanes; D014297:Trimethylsilyl Compounds; D002244:Carbon