solak

About the methylation thing...Have you tried Eschweiler Clarke before? It looks like a nice method for the last step.

This is an old post, but I found it interesting and invented the attached strategy...what do you think? I'm wondering how you've done it.

That's not exactly what I meant. I was thinking about a nucleophilic attack at the Si, releasing the enolate...Although it feels strange drawing it.

Papers would be great One last thing: How reasonable would it be to let the TMS group be attacked? I've seen that with Fluorine, Amine, BuLi and similar reagents. Do you think that would be possible with the enolate? One advantage might be that the carboanion would not have to be formed.

Papers would be great One last thing: How reasonable would it be to let the TMS group be attacked? I've seen that with Fluorine, Amine, BuLi and similar reagents. Do you think that would be possible with the enolate? One advantage might be that the carboanion would not have to be formed.

Thank you so much for your reply. Is your second mechanism is more or less a good guess or have you ever seen a silyl enol ether do that? I've also thought about the carbanion doing what the base normally does so that the product would have a protected alcohol instead of an alcohol in the normal reaction. Another question for me is: How likely would the carbanion be formed if R3 and R4 were methyl groups? The reason why this is is driving me nuts is because I was asked that question in an oral test. He showed me the two compounds with the addition of TiCl4 and I knew that it's Mukaiyama. Then he replaced the Lewis Acid with the Amine and asked me what would happen now. That's when I became totally confused and lost my concentration for the rest of the test. So I'm wondering if someone who's starting his master's thesis should have known what happens....

Hello yall, a professor in an oral test asked me about reacting a silyl enol ether with a michael system and catalytic amounts of a tertiary amine. I was reminded of baylis hillman. He said that this was exactly right and wanted me to draw the product. Unfortunately i didn't understand how that was supposed to work with a silyl enol ether. He said that it would be the same product as with an aldehyde. I don't understand that. I've never seen a silyl enol ether as an electrophile. After some research on the net I couldn't find anything about it. What do you think? Is he wrong? Am I just confused? Any response is appreciated!!