reduction of aldehydes and ketones to alcohols [1] and imines [2] or iminium salts [3] to amines with protic solvents [4]. DOI: 10.1021/cr100084g. Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction In reduction of carbonyls (aldehyde and ketones) to alcohols using NaBH4/Methanol, alkoxides are formed with the Boron which usually gets protonated on addition of water/acid. It is more useful the reduction of unsaturated carbonyl groups H O H O H 1) Li, NH3 liq 2) NH4Cl 99% trans 11 O O OH 1) 2 M 2) 2 ROH 1) 2 M 2) 2 ROH Ketyl radical anion O O O M ROH OH 1) M 2) ROH OH H Pere Romea, 2014. Die Luche-Reduktion ist eine chemische Reaktion, die der selektiven Reduktion von Ketonen neben Aldehyden dient.

Reduction of aldehydes and ketones. However, the activity of NaBH4 can be enhanced by CeCl3 7H2O. The carboxylic acids, esters, amides and nitriles are more resistant towards NaBH 4 [1]. NaBH4 can not reduce esters and their derivatives under ambient conditions, reflux and standing overn ight are necessary. Read "ChemInform Abstract: Regioselectivity in the Reduction of Cyclic Enediones with NaBH4/CeCl3., ChemInform" on DeepDyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips.

Chemical Reviews 2010, 110 (10) , 6104-6143.

The selective 1,2-reduction of enones with sodium borohydride is achieved in combination with CeCl 3. For example, with ethanal you get ethanol: Notice that this is a simplified equation - perfectly acceptable to examiners. Luche Reduction. The Luche reduction can be conducted chemoselectively toward ketone in the presence of aldehyde or toward α,β-unsaturated ketone in the presence of non-conjugated ketone. info. Mechanism of the Luche Reduction. For example, with ethanal you get ethanol: Notice that this is a simplified equation - perfectly acceptable to examiners. CeCl 3 is a selective Lewis acid catalyst for the methanolysis of sodium borohydride. NaBH4, CeCl3.7H2O Applications of CeCl3 as an Environmental Friendly Promoter in Organic Chemistry. Luche reduction is the selective organic reduction of α,β-unsaturated ketones to allylic alcohols with sodium borohydride (NaBH 4) and lanthanide chlorides, mainly cerium(III) chloride (CeCl 3), in methanol or ethanol. The Luche reduction can be conducted chemoselectively toward ketone in the presence of aldehyde or toward α,β-unsaturated ketone in the presence of non-conjugated ketone. The H in square brackets means "hydrogen from a reducing agent". How-ever, the reactivity of NaBH 4 can be enhanced by carrying out the reaction in the presence of certain additives. The reduction of an aldehyde. However, the activity of NaBH4 can be enhanced by CeCl3.7H2O.

Luche reduction is the selective organic reduction of α,β-unsaturated ketones to allylic alcohols with sodium borohydride (NaBH4) and lanthanide chlorides, mainly cerium(III) chloride (CeCl3), in methanol or ethanol. In general terms, reduction of an aldehyde leads to a primary alcohol. Note! The Luche reduction is an organic reaction used to convert an α,β-unsaturated ketone to an allylic alcohol using cerium trichloride, sodium borohydride, and an alcohol solvent. With NaBH4/CeCI3, enedione $ 6573 6574 provided monoalcohols 9, 10, and U in a 1.7:1:1 ratio, respectively, with a regioseleetivity of 73% in favor of reduction of the C-4 alcohol, but NaBH4 alone had given only 11.1 Also, a 1:1 mixture of isomers 12 gave 13, 14, and 15 in a 1.7:1:1.2 ratio, respectively, and therefore 69% regioselectivity in favor of 13 and 14. "Also isolated was the C13-epimer (67 % yield)." The hydride anion is not present during this reaction; rather, these reagents serve as a source of hydride due to the presence of a polar metal-hydrogen bond.

The most common sources of the hydride nucleophile are lithium aluminium hydride (LiAlH 4) and sodium borohydride (NaBH 4). Reductions using NaBH4, LiAlH4. The H in square brackets means "hydrogen from a reducing agent". Devarajulu Sureshkumar, Srinivasamurthy Koutha, Venkataraman Ganesh and Srinivasan Chandrasekaran. NaBH4 can not reduce esters and their derivatives under ambient conditions, reflux and standing overn ight are necessary. My question is what is the function of methanol in this reaction as methanol reacts with NaBH4 to form sodiumtetramethoxyborate and hydrogen gas.