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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.
Luche reduction is the selective organic reduction of α,β-unsaturated ketones to allylic alcohols. [ 1 ] [ 2 ] [ 3 ] The active reductant is described as "cerium borohydride", which is generated in situ from NaBH 4 and CeCl 3 (H 2 O) 7 .
In organic chemistry, carbonyl reduction is the conversion of any carbonyl group, usually to an alcohol. It is a common transformation that is practiced in many ways. [1] Ketones, aldehydes, carboxylic acids, esters, amides, and acid halides - some of the most pervasive functional groups, -comprise carbonyl compounds.
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.
The selectivity of this reagent is illustrated by its reduction of all three methylcyclohexanones to the less stable methylcyclohexanols in >98% yield. Under certain conditions, L-selectride can selectively reduce enones by conjugate addition of hydride, owing to the greater steric hindrance the bulky hydride reagent experiences at the carbonyl ...
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [ 2 ] and later by Fritz Schlotterbeck in 1907. [ 3 ]
Several years later in 1987, E. J. Corey and coworkers developed the reaction between chiral amino alcohols and borane (BH 3), generating oxazaborolidine products which were shown to rapidly catalyze the enantioselective reduction of achiral ketones in the presence of BH 3 •THF. [2] [3] The CBS reduction has since been utilized by organic ...
Ketones with two available α-methylene positions react more quickly at the least hindered position.: [1] Allylic oxidation can be predicted by the substitution pattern on the olefin. In the case of 1,2-disubstituted olefins, reaction rates follow CH > CH 2 > CH 3: Geminally-substituted olefins react in the same order of reaction rates as above ...