[jaydd]

Hi ..
I got a little problem .. I hope somebody can help me out.. I need to figure out the detailed mechanism for Tamiflu synthesis, and I am kinda stuck on this part...
any help would be great..
Thanks
 Jay

[movies]

That's a tough one!  So what kind of reactions can you think of between palladium and an allyl group?

[victor]

I think that the reaction starts with protonation on N atom, so allyl group will be released and get attached with methoxide ionsso it will form allyl methyl ether. And for the Pd catalyst, I think I've ever read in my chem book that it's needed to speed up ether (allyl methyl ether) synthesis...that's what I think and because I'm not a chemie studet, please anyone correct me if I'm wrong..

Victor

[movies]

Not quite, but a good thought.  The allyl part doesn't actually fall off until the second step though.

Anyone else have any ideas?  This is a really great question and I don't want to give it away!

[victor]

One thing that bothering me...N atom has a pair of free electron and I guess that protonation by 1 H+ ion would only make it become amonium salt... any idea about this??

[movies]

Where would that get you?  The acid is added in the second step, so what do you think could happen in the first step to make the molecule more reactive toward acid?

[victor]

Ohh...I think it's just only a one-step reaction so I start the reaction with protonation of N atom..
I start to confuse then if addition by acid is done in the second step, because without acid, CH₃OH will only dissosiates a little become CH₃O^_ and H⁺..so, how could protonation to N atom can be done???

[movies]

Maybe that is a hint that the first step isn't protonation of the N.   

[Organishe]

okay I'm going to have a crack at this:

1st step: complexation of the allyl group to the paladium catalyst. Frankly, I'm not quite sure what this will accomplish, but let's roll with it    totally off the wall guess here, but perhaps since this will weaken the pi bond, it will promote an S_N2' reaction for our second step.

2nd step: protonation of the nitrogen, followed by either some kind of S_N2' or S_N2 by water to form the target amine plus allyl alcohol.

[movies]

I like your idea with Pd in the first step, but the Pd is gone by the second step.  What could happen once the Pd is complexed to the olefin of the allyl group?