hi, stuck on something i did, that i cant explain. when i attempted the aldol reaction of 3-(benzyloxy)-2,2-dimethylpropanal it didnt work. my old supervisor said it was because it underwent a wagner meerwein rearrangement (one of the methyl migrated). to me from the nmr i couldnt tell how he knew because it looked like a mess. how and why would this happen. i have looked at the mechanism of this rearrangement and understand it sort of but why in this case. how could i reason it for my thesis. ps the aldols that were attempted were, evan's oxazolidinone using boron triflate, oppolzer sultam using ticl4 and then a direct crossed aldol using proline and propanal. thanks in advance. he also said this was common for this type of aldehyde (one with gem methyls)??
