reductive hydroxymetylation
Hello everyone! I am currently trying to reproduce reaction b in this scheme. It appears that the mechanism involves a lithium reduction of the enone to form an enolate, which is then trapped with TMSCl to yield the silyl enol ether, followed by a Mukaiyama aldol reaction.
However, I am having trouble trapping the enolate with TMSCl. The major product I'm obtaining is simply the saturated ketone (reduction of the double bond). Could this be due to trace moisture in my reaction environment protonating the enolate before silylation can occur? I even dry my ammonia gas from the ammonia tank by passing through a CaO column but the result is still unpleasant. I would greatly appreciate any advice or troubleshooting tips from anyone who has experience with this type of transformation. Thank you very much.