I'm interest in knowing what is the best way to reduce selectively some insaturated functional groups in a molecule.
The example that I have in mind is one compound with one alkene group and an aldehyde carbonyl.
What's the best way of just hydrogenating the alkene? Do I need to protect carbonyl with, for example, ethylenglycol + TsOH, then reduce double bond (with H2/Pd), and then recover aldehyde in acid media?
Or is there any reagent that allow to do this reduction selectively in one step?
I know that LiAlH4 wont hydrogenate alkene, just will reduce aldehyde, but H2/Pd will reduce both. Is there any easy way to do exactly the opposite?