[Markovnikov]

So we've been going through Metal assisted Nu-attacks on olefins and we've always handled allylic carbonates and allylic acetates separately. In this case, we have both an allylic carbonate and an allylic acetate, so which side will the Nu be attacked? If there were no base, I'd say that it'd probably be at the allylic carbonate since you form a base in situ... but now with NaH, I have no idea which is faster...

What about stereoselectivity?

For the acetate, the Nu will end up on the same side as the acetate due to the fact that Pd coordinates to the olefin from the opposite side and oxidatively adds, the Nu would then attack on the least hindered side (opposite side of the Pd).

For the allylic carbonate I have no idea.  

Thanks for any help/insight possible!

[movies]

The same stereochemical reasoning holds with allylic carbonates and stabilized nucleophiles like the one you have.  As far as the selectivity in oxidative addition, empirically carbonates tend to react faster than allylic esters.

[Markovnikov]

Thanks for your help movies!