In the original Akabori reaction, an amino acid condenses with an aldehyde. I am wondering if it would be feasible to condense the amino acid with
other carbonyls.
I am assuming that the carboxyl is ionized, and the oxygen donates a pair to the carboxyl carbon, and the rest of the amino acid is the leaving group.
The carbanion attacks the aldehyde.
I would like to synthesis alpha-amino ketones by condensing an amino acid with an ester. I can see yields diminished by amide formation and
condensation of the ketone with the amine again. Perhaps protection of the amine group into an amide would increase yields.
Incidentally, can anyone recommend a good linux application for drawing mechanisms? It's hard to explain this stuff without them. I used to
have Chemdraw and the Merck index, but i don't sanction software theft any more :\docberto - 3-6-2005 at 20:11
I used XDrawChem to draw the mechanism of the essential intermediate.
Sandmeyer - 22-6-2005 at 04:14
How good does this reaction work IRL, has anyone tried it? I've seen some japaneese papers, but it is impossible to make sense out of them.mykhal - 26-6-2005 at 10:29
Quote:
Incidentally, can anyone recommend a good linux application for drawing mechanisms?
You may try bkchem.CherrieBaby - 16-11-2005 at 23:49
I don't have anything on this specifically but here's a page of an old paper I found in my notes (page 1950 is just 'lost'
somewhere).
