biomechem - 9-5-2018 at 07:27
Is it possibile to predict which of these reactions will take a place with α-amino ketones? If it is then how to do it?
Also would sodium bisulfite be sufficient for protecting ketone group?
[Edited on 9-5-2018 by biomechem]
CaptainMolo - 10-5-2018 at 09:16
I honestly don’t even know those two reactions very well, but that last part sounds dubious because bisulfite adducts can be broken quite easily
with dilute acid or alkaline solutions. I don’t know if that’s helpful at all but that’s what came to mind when I saw that.
After looking up the two reactions, I can say that for the Eschweiler-Clarke reaction, the example given mentioned formic acid, which would likely
break the adduct. The Leuckart reaction mentions formamide which is alkaline, but I don’t know if it’s alkaline enough to break the adduct.
Do you currently have a synthesis planned that would encounter this scenario, or is this purely theoretical? If you’re doing a real synthesis I
would very much like to hear how it went. It sounds interesting.