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Borane–tetrahydrofuran is an adduct derived from borane and tetrahydrofuran (THF). These solutions, which are colorless, are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds. A common alternative to BHF•THF is borane–dimethylsulfide, which has a longer shelf life and effects similar ...
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. [1] The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been.
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.
Hydroboration proceeds via a four-membered transition state: the hydrogen and the boron atoms added on the same face of the double bond. Granted that the mechanism is concerted, the formation of the C-B bond proceeds slightly faster than the formation of the C-H bond.
Borane dimethylsulfide (BMS) is a chemical compound with the chemical formula BH 3 ·S(CH 3) 2.It is an adduct between borane molecule (BH 3) and dimethyl sulfide molecule (S(CH 3) 2).
Molecular species BH 3 is a very strong Lewis acid.It can be isolated in the form of various adducts, such as borane carbonyl, BH 3 (CO). [11]Molecular BH 3 is believed to be a reaction intermediate in the pyrolysis of diborane to produce higher boranes: [5]
The cationic sodium ion, [Na] +, interacts with the anionic cyanoborohydride ion, [BH3(CN)] −. The anionic component of the salt is tetrahedral at the boron atom. The electron-withdrawing cyanide substituent draws electron density away from the negatively charged boron; thus, reducing the electrophilic capabilities of the anionic component. [ 2 ]
Generally, 2-10 mol% of this catalyst is used along with borane-tetrahydrofuran (THF), borane-dimethylsulfide, borane-N,N-diethylaniline, or diborane as the borane source. Enantioselective reduction using chiral oxazaborolidine catalysts has been used in the synthesis of commercial drugs such as ezetimibe and aprepitant.