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 corresp...

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Bibliographic Details
Published in:Organic letters 2008-03, Vol.10 (5), p.877-880
Main Authors: Song, Jinhua J, Tan, Zhulin, Reeves, Jonathan T, Fandrick, Daniel R, Yee, Nathan K, Senanayake, Chris H
Format: Article
Language:English
Subjects:
Catalysis
Combinatorial Chemistry Techniques
Ethers - chemical synthesis
Hydrocarbons - chemistry
Ketones - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
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Summary: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 °C in THF.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol703025b