N-heterocyclic carbene-catalyzed silyl enol ether formation.
N-Heterocyclic carbenes (NHCs) were found to catalyze the silyl transfer from trialkylsilyl ketene acetals to ketones. In the presence of a catalytic amount of NHC 3 (IAd, 0.1 to 5 mol %), a series of enolizable ketones as well as cyclohexanecarboxaldehyde were efficiently converted into the corresponding silyl enol ethers at 23 degrees C in THF.
Song
Jinhua J
JJ
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. jeff.song@boehringer-ingelheim.com
Tan
Zhulin
Z
Reeves
Jonathan T
JT
Fandrick
Daniel R
DR
Yee
Nathan K
NK
Senanayake
Chris H
CH
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000138:chemical synthesis*; D006838:Hydrocarbons / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D004987:Ethers; D006838:Hydrocarbons; D007659:Ketones; D017646:Organosilicon Compounds; C030011:carbene; D008697:Methane