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Luche Reduction
The Luche reduction is a regioselective reduction to afford allyl alcohols from α,β-unsaturated ketones. When α,β-unsaturated ketones are reduced with sodium borohydride (NaBH4), 1,4-reduction, not 1,2-reduction, preferentially occurs. It is considered that since the hydride of NaBH4 is a “soft” nucleophile, the reaction proceeds at the β-position of the carbonyl compounds, which prefers a “soft” nucleophile. However, the hydride turns to “hard” in the presence of cerium(III) chloride and an alcohol solvent, resulting in preferential 1,2-reduction. Incidentally, an aldehyde is not reduced using this method because it forms an acetal, which is inert under these conditions.
- Reagents:
- Sodium borohydride, Cerium(III) chloride anhydrous
- Reactants:
- α,β-Unsaturated ketones
- Products:
- Allyl alcohols
- Scheme:
-
- Original literature:
-
- Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones
- Reduction of natural enones in the presence of cerium trichloride
- Review literature:
-
- Application of lanthanide reagents in organic synthesis
- Applications of CeCl3 as an Environmental Friendly Promoter in Organic Chemistry
