How to reduce α, β-unsaturated carbonyl compounds
المؤلف:
Jonathan Clayden , Nick Greeves , Stuart Warren
المصدر:
ORGANIC CHEMISTRY
الجزء والصفحة:
ص536-537
2025-06-21
321
It should not now surprise you that regioselective reduction of the C=C double bond of an α, β-unsaturated carbonyl compound is best done using catalytic hydrogenation as the C=C bond is more susceptible to hydrogenation than the C=O bond. The flavouring compound known as raspberry ketone is made by this method.
But what if you want instead to reduce the C=O group selectively? You should immediately think of using NaBH4. we pointed out that hydride reducing agents in general are not good choices for the selective reduction of the C=O bond of unsaturated carbonyl compounds because they tend to add to the double bond as well, giving fi rst the saturated carbonyl compound, which is then reduced to the alcohol. The way to get regioselective addition directly to the carbonyl group is to use NaBH4 in the presence of a hard, Lewis-acidic metal salt, such as CeCl3. This combination of reagents is known as the Luche reduction.
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