The Student Room Group

Selective reduction of alkene

Hi guys,

I have a small problem I need a hand with. How would one selectively reduce the alkene in a structure with an aldehyde and an alkene. I should mention that the alkene and the carbonyl of the aldehyde are not conjugated. So an alkene somewhere in the molecule and then an aldehyde far from it.

Thanks
Any takers?
Reply 2
I can't at the top of my head think of any reagent which would selectively reduce an alkene over an aldehyde but what you could do is protect the aldehyde first with ethylene glycol to form the acetal. Now you can use something like borane to reduce the alkene and finally deprotect the aldehyde with aqueous acid.
There are catalysts/conditions to achieve selective reduction in the way you want, but in reality this would probably take a fair amount of work in order to do that for a non-investigated compound. I'd go with Kyris' suggestion for a 'less hassle' approach :p:

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