Hintermann, Lukas; Schmitz, Marco; Maltsev, Oleg V.; Naumov, Pance published the artcile< Organocatalytic stereoisomerization versus alkene isomerization: catalytic asymmetric synthesis of 1-hydroxy-trans-2,5-diphenylphospholane 1-oxide>, HPLC of Formula: 112-63-0, the main research area is organocatalysis stereoisomerization; catalytic asym synthesis hydroxydiphenyl phospholane oxide; McCormack cycloaddition diarylbutadiene dialkylamino dichlorophosphine; crystal mol structure hydroxydiphenyl phospholane oxide derivative.
The potential for an organocatalytic asym. stereoisomerization or alkene isomerization as atom-economic reaction with minimal structural change was investigated. The McCormack cycloaddition of 1,4-diarylbuta-1,3-dienes with (dialkylamino)dichlorophosphine and aluminum trichloride gives meso-2,5-diaryl-1-(dialkylamino)-1-oxo-2,5-dihydro-1H-phospholes, which were identified as suitable substrates for asym. isomerization to (1R,5R)-2,5-diaryl-1-(dialkylamino)-1-oxo-4,5-dihydro-1H-phospholes in the presence of bifunctional organocatalysts (cinchona alkaloids, Takemoto catalyst) in up to 91% ee and quant. yield. The substrate range and the mechanism of the catalysis were studied. The reaction involves proton abstraction by the base, but a primary deuterium KIE is absent. Enriched (1R,5R)-1-(diethylamino)-1-oxo-2,5-diphenyl-4,5-dihydro-1H-phosphole was hydrolyzed to (5R)-1-hydroxy-1-oxo-2,5-diphenyl-4,5-dihydro-1H-phosphole, which was hydrogenated diastereoselectively under dissolving metal conditions to give (2R,5R)-1-hydroxy-1-oxo-2,5-diphenylphospholane (Fiaud’s acid) in preference to meso-1-hydroxy-1-oxo-2,5-diphenylphospholane. An asym. catalytic total synthesis of Fiaud’s acid, which is a building block for chiral phospholane synthesis, has been realized in five steps from thiophene, using nickel-catalyzed Wenkert arylation, McCormack cycloaddition, asym. dihydro-1H-phosphole isomerization, hydrolysis, and diastereoselective hydrogenation.
Synthesis published new progress about Bifunctional catalysts, organocatalysts. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, HPLC of Formula: 112-63-0.
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