# Synthetic options for selective hydroxylation at terminal position

Are there any synthetic options to add a hydroxyl group at the terminal position to the bicyclo compound below? What might be reactions worth trying, any idea? Or is this a lost cause?

## 1 Answer

Or is this a lost cause?

I don't think so. This looks like a good candidate for an allylic oxidation with selenium dioxide, look here for some examples.

• Thanks Klaus! That helps. I will explore that. Would you expect this to form as a side product? i.imgur.com/9hDnzzv.png Apr 7 '16 at 17:58
• @curious_cat No, not really. If I remember correctly, the transformation is was regioselective on geraniol derivatives, but the yields differed a lot, depending on the kind of derivative (acetate, sulfone, thiophenyl ether) used. You might want to run a search with the keywords Sharpless allylic oxidation, selenium dioxide, and geranyl acetate to find some more reliable references. Quite often, the reaction is performed with catalytic amounts of $\ce{SeO2}$ and tert.-butyl hydroperoxide. Apr 7 '16 at 19:06