113666-64-1Relevant articles and documents
High-efficiency and minimum-waste continuous kinetic resolution of racemic alcohols by using lipase in supercritical carbon dioxide
Matsuda, Tomoko,Watanabe, Kazunori,Harada, Tadao,Nakamura, Kaoru,Arita, Yoshitaka,Misumi, Yukibiro,Ichikawa, Shinichiro,Ikariya, Takao
, p. 2286 - 2287 (2004)
A novel continuous-flow scCO2 process for kinetic resolution of racemic alcohols can be performed with an immobilized lipase to lead to a quantitative mixture of the corresponding optically active acetates with up to 99% ee and unreacted alcohols with up to 99% ee, in which the productivity of the optically active compounds was improved by over 400 times compared to the corresponding batch reaction using scCO2.
SELECTIVE REMOVAL OF TETRAHYDROPYRANYL ETHERS IN THE PRESENCE OF TERT-BUTYLDIMETHYLSILYL ETHERS WITH MAGNESIUM BROMIDE IN ETHER
Kim, Sunggak,Park, Jung Ho
, p. 439 - 440 (1987)
It has been found that tetrahydropyranyl ethers are cleanly and selectively deprotected in the presence of tert-butyldimethylsilyl ethers with magnesium bromide in ether.
Stereoselective opening of acetals derived from dimethyl tartrate
Guindon,Simoneaua,Yoakima,Gorysa,Lemieuxa,Ogilvie
, p. 5453 - 5456 (1991)
Acetals of dimethyl tartrate can be used to prepare optically active secondary alcohols from the corresponding aldehydes. The key step involves treatment of the acetals with dialkylboron bromides and higher order cuprates. The process involves an unusual
Highly chemo-, diastereo-, and enantioselective reduction of 1,2-dialkyl-3-aryl-1,3-diketones for preparation of aldol-type compounds
Ohtsuka, Yuhki,Koyasu, Kiichirou,Miyazaki, Daichi,Ikeno, Taketo,Yamada, Tohru
, p. 3421 - 3424 (2001)
Equation presented Highly chemo-, diastereo-, and enantioselective borohydride reduction of 2-substituted-1,3-diketones was achieved in the presence of the optically active β-ketoiminato cobalt complex catalysts to afford the optically active 2-substituted-3-hydroxyketones. The present catalytic and enantioselective reduction could provide an alternative potential for preparation of optically active anti-aldol-type compounds.
Phosphine-NHC Manganese Hydrogenation Catalyst Exhibiting a Non-Classical Metal-Ligand Cooperative H2 Activation Mode
Buhaibeh, Ruqaya,Filippov, Oleg A.,Bruneau-Voisine, Antoine,Willot, Jérémy,Duhayon, Carine,Valyaev, Dmitry A.,Lugan, No?l,Canac, Yves,Sortais, Jean-Baptiste
supporting information, p. 6727 - 6731 (2019/04/17)
Deprotonation of the MnI NHC-phosphine complex fac-[MnBr(CO)3(κ2P,C-Ph2PCH2NHC)] (2) under a H2 atmosphere readily gives the hydride fac-[MnH(CO)3(κ2P,C-Ph2PCH2NHC)] (3) via the intermediacy of the highly reactive 18-e NHC-phosphinomethanide complex fac-[Mn(CO)3(κ3P,C,C-Ph2PCHNHC)] (6 a). DFT calculations revealed that the preferred reaction mechanism involves the unsaturated 16-e mangana-substituted phosphonium ylide complex fac-[Mn(CO)3(κ2P,C-Ph2P=CHNHC)] (6 b) as key intermediate able to activate H2 via a non-classical mode of metal-ligand cooperation implying a formal λ5-P–λ3-P phosphorus valence change. Complex 2 is shown to be one of the most efficient pre-catalysts for ketone hydrogenation in the MnI series reported to date (TON up to 6200).
Hydrogenation of Carbonyl Derivatives Catalysed by Manganese Complexes Bearing Bidentate Pyridinyl-Phosphine Ligands
Wei, Duo,Bruneau-Voisine, Antoine,Chauvin, Téo,Dorcet, Vincent,Roisnel, Thierry,Valyaev, Dmitry A.,Lugan, No?l,Sortais, Jean-Baptiste
supporting information, p. 676 - 681 (2017/12/26)
Manganese(I) catalysts incorporating readily available bidentate 2-aminopyridinyl-phosphine ligands achieve a high efficiency in the hydrogenation of carbonyl compounds, significantly better than parent ones based on more elaborated and expensive tridentate 2,6-(diaminopyridinyl)-diphosphine ligands. The reaction proceeds with low catalyst loading (0.5 mol%) under mild conditions (50 °C) with yields up to 96%. (Figure presented.).
Rhenium and manganese complexes bearing amino-bis(phosphinite) ligands: Synthesis, characterization, and catalytic activity in hydrogenation of ketones
Li, Haoran,Wei, Duo,Bruneau-Voisine, Antoine,Ducamp, Maxime,Henrion, Micka?l,Roisnel, Thierry,Dorcet, Vincent,Darcel, Christophe,Carpentier, Jean-Fran?ois,Soulé, Jean-Fran?ois,Sortais, Jean-Baptiste
supporting information, p. 1271 - 1279 (2018/04/30)
A series of rhenium and manganese complexes supported by easily accessible and easily tunable amino-bisphosphinite ligands was prepared and characterized by NMR and IR spectroscopy, HR mass spectrometry, elemental analysis, and X-ray diffraction studies. These complexes have been tested in the hydrogenation of ketones. Notably, one of the rhenium complexes, bearing an NH moiety, proved significantly more active than the rest of the series. The reaction proceeds well at 120 °C, under 50 bar of H2, in the presence of 0.5 mol % of catalyst and 1 mol % of tBuOK. Interestingly, activation of the precatalyst could be followed stepwise by NMR and a rhenium hydride was characterized by X-ray diffraction studies.
Enzymatic chemical transformations of aldehydes, ketones, esters and alcohols using plant fragments as the only biocatalyst: Ximenia americana grains
da Silva, Romézio Alves Carvalho,de Mesquita, Bruna Marques,de Farias, Iolanda Frota,do Nascimento, Patrícia Georgiana Garcia,de Lemos, Telma Leda Gomes,Queiroz Monte, Francisco José
, p. 187 - 194 (2018/01/05)
The present study demonstrated the ability of Ximenia american as a biocatalyst in reduction, hydrolysis and esterification reactions. The reduction reactions of aldehydes and ketones, ester hydrolysis and esterification of alcohols were carried out with interesting results. Reduction of ketones afforded yields of 6–60% with ee in the range of 35–>99% and that of aldehydes in yields of 51–99%. On the other hand, ester hydrolysis afforded yields of 58–98% with ee in the range 34–87%, while esterification of alcohols in 18–99% yields. Experimental conditions for all reactions have been defined using standard substrates as indicated in results and discussion. Some of the products are the potential building blocks for the synthesis of molecules which are of pharmaceutical and agrochemical importance.
Hydrogenation of Carbonyl Derivatives with a Well-Defined Rhenium Precatalyst
Wei, Duo,Roisnel, Thierry,Darcel, Christophe,Clot, Eric,Sortais, Jean-Baptiste
, p. 80 - 83 (2017/01/17)
The first efficient and general rhenium-catalyzed hydrogenation of carbonyl derivatives was developed. The key to the success of the reaction was the use of a well-defined rhenium complex bearing a tridentate diphosphinoamino ligand as the catalyst (0.5 mol %) at 70 °C in the presence of H2 (30 bar). The mechanism of the reaction was investigated by DFT(PBE0-D3) calculations.
Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst
Bruneau-Voisine, Antoine,Wang, Ding,Dorcet, Vincent,Roisnel, Thierry,Darcel, Christophe,Sortais, Jean-Baptiste
supporting information, p. 3656 - 3659 (2017/07/15)
A very simple and inexpensive catalytic system based on abundant manganese as transition metal and on an inexpensive phosphine-free bidendate ligand, 2-(aminomethyl)pyridine, has been developed for the reduction of a large variety of carbonyl derivatives with 2-propanol as hydrogen donor. Remarkably, the reaction proceeds at room temperature with low catalyst loading (down to 0.1 mol %) and exhibits a good tolerance toward functional groups. High TON (2000) and TOF (3600 h-1) were obtained.
