I cannot think of any way of inserting a palladium, platinum, or nickel catalyst into the more hindered side. If one wished to get the trans product from alpha-pinene knowing that the top face is sterically hindered, then I'd try a radical addition of HBr or just add bromine. For HBr, I'd expect the hydrogen to add from the least hindered side. The reductive hydrobromination would give the trans-pinane.