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Enantioselective ketone reductions convert prochiral ketones into chiral, non-racemic alcohols and are used heavily for the synthesis of stereodefined alcohols. [ 1 ] Carbonyl reduction, the net addition of H 2 across a carbon-oxygen double bond, is an important way to prepare alcohols.
For the α,β unsaturated systems 10-12, efficient reduction of the ketone occurs despite the possible side reaction of hydroboration of the C-C unsaturated bond. The CBS reduction has also been shown to tolerate the presence of heteroatoms as in ketone 13 , which is capable of coordinating to the borane.
The Luche reduction can be conducted chemoselectively toward ketone in the presence of aldehydes or towards α,β-unsaturated ketones in the presence of a non-conjugated ketone. [5] An enone forms an allylic alcohol in a 1,2-addition, and the competing conjugate 1,4-addition is suppressed.
The second reaction is the organic reduction of 1,2-diphenyl-1-propanone 2 with lithium aluminium hydride, which results in the same reaction product as above but now with preference for the erythro isomer (2a). Now a hydride anion (H −) is the nucleophile attacking from the least hindered side (imagine hydrogen entering from the paper plane).
The final step in the reduction of carboxylic acids and esters is hydrolysis of the aluminium alcoxide. [8] Esters (and amides) are more easily reduced than the parent carboxylic acids. Their reduction affords alcohols and amines, respectively. [9] The idealized equation for the reduction of an ester by lithium aluminium hydride is:
The McMurry reaction of benzophenone. The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to form an alkene using a titanium chloride compound such as titanium(III) chloride and a reducing agent. The reaction is named after its co-discoverer, John E. McMurry.
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[Al H 4] or LiAlH 4.It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. [4]
The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. [1] It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. [2] [3] [4] Bouveault and Blanc demonstrated the reduction of ethyl oleate and n-butyl oleate to oleyl alcohol. [5]