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Lithium borohydride (LiBH 4) is a borohydride and known in organic synthesis as a reducing agent for esters.Although less common than the related sodium borohydride, the lithium salt offers some advantages, being a stronger reducing agent and highly soluble in ethers, whilst remaining safer to handle than lithium aluminium hydride.
It has also been shown to reduce aromatic esters to the corresponding alcohols as shown in eq 6 and 7. LiBHEt 3 also reduces pyridine and isoquinolines to piperidines and tetrahydroisoquinolines respectively. [7] The reduction of β-hydroxysulfinyl imines with catecholborane and LiBHEt 3 produces anti-1,3-amino alcohols shown in (8). [8]
LiAl(OCH 2 R) 2 (OR') + 4 H 2 O → LiAl(OH) 4 + 2 HOCH 2 R + 2 HOR' Sodium borohydride can, under some circumstances, be used for ester reduction, especially with additives. [1] Forming aldehydes from carboxylic acid derivatives is challenging because weaker reducing agents (NaBH 4) are often very slow at reducing esters and carboxylic acids ...
An ester of carboxylic acid.R stands for any group (organic or inorganic) and R′ stands for organyl group.. In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group (−OH) of that acid is replaced by an organyl group (−R).
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.
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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 ...