1-Dimethyl(phenyl)silylpentan-3-one(4),3-dimethyl(phenyl)silylcyclopentanone(10) and 3-dimethyl (phenyl)silylcyclohexanone (16) are deprotonated by lithium di-isopropylamide in favour of enolate formation away from the silyl group to the extent of 70 : 30, 70 : 30, and > 95 : 5, respectively. The effect of the silyl group appears to be largely steric in origin.
W. Engel, I. Fleming and R. H. Smithers, J. Chem. Soc., Perkin Trans. 1, 1986, 1637 DOI: 10.1039/P19860001637
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