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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]
The Evans–Tishchenko reaction is the diastereoselective reduction of β-hydroxy ketones to the corresponding 1,3-anti diol monoesters. The reaction employs a Lewis acid, often samarium iodide, and an aldehyde. It was first described in 1990 by David A. Evans and Amir Hoveyda, as a development of the well-known Tishchenko reaction discovered ...
The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde in the presence of an alkoxide.The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective catalysts for the reaction.
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 industrial synthesis of diborane involves the reduction of BF 3 by sodium hydride (NaH), lithium hydride (LiH) or lithium aluminium hydride (LiAlH 4): [11] 8 BF 3 + 6 LiH → B 2 H 6 + 6 LiBF 4. Lithium hydride used for this purpose must be very finely powdered to avoid the formation of a passivating lithium tetrafluoroborate layer on the ...
In addition, transformations with chiral auxiliaries tend to be versatile and very well-studied, allowing the most time-efficient access to enantiomerically pure products. [ 2 ] Furthermore, [ 7 ] the products of auxiliary-directed reactions are diastereomers , which enables their facile separation by methods such as column chromatography or ...
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]