Im reading some papers on stereoselective synthesis and one thing makes me wonder, how can i control which enol I make?
For example, if I have methy-ethyl ketone and I add base, I think two products will be formed: the one where the methyl group is deprotonated and the one where methylene group is deprotonated. I suppose the deprotonation at methyl is faster because the protons are more acidic, while the deprotonation at methylene gives more stable product because there are more hydrogens in hyperconjugation with the double bond. Is that right? Does it mean that if I let the deprotonation run longer, the enol where the methylene group is deprotonated will dominate in the mixture?
Or are there other ways how to force one or the other enol to dominate?