1517-70-0Relevant academic research and scientific papers
A New Class of "Tethered" Ruthenium(II) Catalyst for Asymmetric Transfer Hydrogenation Reactions
Hannedouche, Jerome,Clarkson, Guy J.,Wills, Martin
, p. 986 - 987 (2004)
Ruthenium dimer 4 is converted directly to monomeric asymmetric transfer hydrogenation catalyst 2 under the conditions employed for ketone reduction. Using 0.25 mol % of either 4 or 0.5 mol % of 2 in formic acid/triethylamine, it is possible to achieve ketone reduction in quantitative conversion and with ee's as high as 98%. Complex 2 is a robust "single-reagent" catalyst which offers significant scope for modification toward specific substrates. The synthesis and applications of an analogous complex derived from (1R,2S)-norephedrine are also described. Copyright
Multi-substrate screening for lipase-catalyzed resolution of arylalkylethanols with succinic anhydride as acylating agent
Debbeche, Hanane,Toffano, Martial,Fiaud, Jean-Claude,Aribi-Zouioueche, Louisa
, p. 319 - 324 (2010)
CAL-B lipase-catalyzed resolution of a number of arylalkylethanols using succinic anhydride as acylating agent has been performed to evaluate the corresponding enantioselectivity factors. Then "one-pot multi-substrate screening" reactions involving two-and four-substrate mixtures were carried out and evaluation of the enantioselectivity factors for each alcohol was undertook by a single-run analysis. It was concluded that the alcohols in the mixture behave independently, validating the "one-pot multisubstrate screening" for a rapid evaluation of the enantioselectivity of the kinetic resolution process for each individual substrate.
Biocatalytic anti-Prelog stereoselective reduction of 4′- methoxyacetophenone to (R)-1-(4-methoxyphenyl)ethanol with immobilized Trigonopsis variabilis AS2.1611 cells using an ionic liquid-containing medium
Lou, Wen-Yong,Wang, Wei,Smith, Thomas J.,Zong, Min-Hua
, p. 1377 - 1384 (2009)
The biocatalytic anti-Prelog enantioselective reduction of 4′-methoxyacetophenone (MOAP) to (R)-1-(4-methoxyphenyl)ethanol {(R)-MOPE} using immobilized Trigonopsis variabilis AS2.1611 cells was, for the first time, successfully conducted in an ionic liqui
Novel recoverable catalysts for asymmetric transfer hydrogenation
He, Wei,Zhang, Bang-Le,Jiang, Ru,Liu, Peng,Sun, Xiao-Li,Zhang, Sheng-Yong
, p. 5367 - 5370 (2006)
9-Amino(9-deoxy)epiquinine and 9-amino(9-deoxy)epicinchonine were applied in asymmetric transfer hydrogenation of aromatic ketones in both iridium and rhodium catalytic systems using i-propanol as the hydrogen source. Good to excellent conversions and ena
New Homochiral Binaphthol-Modified Organolanthanide Reagents for the Enantioselective Addition to Aldehydes
Chibale, Kelly,Greeves, Nicholas,Lyford, Lisa,Pease, J. Elizabeth
, p. 2407 - 2410 (1993)
Optically active secondary alcohols were obtained in high chemical yield and optical purity (up to 85percent ee) from the lanthanide-mediated enantioselective addition of alkyl nucleophiles to aromatic aldehydes.
Efficient heterogeneous catalytic systems for enantioselective hydrogenation of prochiral carbonyl compounds
Ghosh, Anirban,Kumar, Rajiv
, p. 386 - 396 (2004)
A proficient heterogeneous catalyst system for stereoselective hydrogenation of carbonyl compounds was synthesized, involving anchoring of RuII-phosphine-diamine complexes on the inner surfaces of organo-functionalized mesoporous MCM-41 and MCM-48 materials. Powder XRD and TEM experiments reveal highly ordered hexagonal and cubic patterns of the organically modified MCM-41 and MCM-48 materials, respectively, even after incorporation of Ru complexes. Moreover, the integrity of the Ru complexes was retained after anchoring into the mesoporous hosts, which was supported from FTIR, 31P CP MAS NMR, and XPS analyses. This new heterogeneous catalyst shows promising activity and selectivity in the enantioselective hydrogenation of prochiral ketones. The effects of reaction time, temperature, and hydrogen pressure on the catalytic activity and enantioselectivity were studied in detail. As high as 95-99% ee could be obtained using these solid catalysts under heterogeneous reaction conditions. The anchored solid catalysts can be recycled effectively and reused several times without any loss in activity and selectivity.
Facile synthesis of a mesoporous silica-supported catalyst for Ru-catalyzed transfer hydrogenation of ketones
Liu, Guohua,Yao, Mei,Zhang, Fang,Gao, Yan,Li, Hexing
, p. 347 - 349 (2008)
A convenient method for preparation of a mesoporous silica-supported chiral catalyst by postgrafting a homogeneous catalyst on SBA-15 was developed and its application in the asymmetric transfer hydrogenation of aromatic ketones was investigated. The Roya
Screening of chiral ferrocenyl amino alcohols as ligands for ruthenium-catalysed transfer hydrogenation of ketones
Patti, Angela,Pedotti, Sonia
, p. 597 - 602 (2003)
A variety of ferrocenyl amino alcohols possessing central chirality have been screened as ligands for ruthenium(II)-catalysed transfer hydrogenation of acetophenone using 2-propanol in the presence of KOH as the hydrogen source. Enantiomerically enriched
Immobilization of marine fungi on silica gel, silica xerogel and chitosan for biocatalytic reduction of ketones
Rocha, Lenilson Coutinho,De Souza, Adriano Lopes,Rodrigues Filho, Ubirajara Pereira,Campana Filho, Sergio Paulo,Sette, Lara Duraes,Porto, Andre Luiz Meleiro
, p. 160 - 165 (2012)
The scanning electron microscopy (SEM) analysis showed that whole living hyphal of marine fungi Aspergillus sclerotiorum CBMAI 849 and Penicillium citrinum CBMAI 1186 were immobilized on support matrices of silica gel, silica xerogel and/or chitosan. P. citrinum immobilized on chitosan catalyzed the quantitative reduction of 1-(4-methoxyphenyl)-ethanone (1) to the enantiomer (S)-1-(4-methoxyphenyl)-ethanol (3b), with excellent enantioselectivity (ee > 99%, yield = 95%). Interestingly, ketone 1 was reduced with moderate selectivity and conversion to alcohol 3b (ee = 69%, c 40%) by the free mycelium of P. citrinum. This free mycelium of P. citrinum catalyzed the production of the (R)-alcohol 3a, the antipode of the alcohol produced by the immobilized cells. P. citrinum immobilized on chitosan also catalyzed the bioreduction of 2-chloro-1-phenylethanone (2) to 2-chloro-1-phenylethanol (4a,b), but in this case without optical selectivity. These results showed that biocatalytic reduction of ketones by immobilization hyphal of marine fungi depends on the xenobiotic substrate and the support matrix used.
Preparation of microgel-supported chiral catalysts and their application in the asymmetric hydrogenation of aromatic ketones
Deng, Jia,Lu, Cuifen,Yang, Guichun,Chen, Zuxing
, p. 378 - 382 (2012)
An enantiomerically pure chiral monomer (S,S)-2 was prepared and copolymerized with styrene and four different cross-linkers to produce four distinct microgel-supported chiral TsDPEN derivatives. These chiral copolymers were allowed to form complexes with
