34666-01-8Relevant academic research and scientific papers
Model Studies on the Enzyme-Regulated Stereodivergent Cascade Passerini Reaction
Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Samsonowicz-Górski, Jan,Wilk, Monika
supporting information, p. 4161 - 4165 (2021/08/24)
The synthesis of chiral α-acyloxy carboxamides containing two stereogenic centers continues to be a challenging field of organic chemistry. Herein, we have proposed and proved the feasibility of an enzyme regulated-cascade reaction, which using the same substrates enables the formation of individual stereoisomers of α-acyloxy carboxamides with up to 99 % ee. The access to the individual stereoisomeric products has been achieved by a combination of the enzymatic kinetic resolution of racemic vinyl esters, subsequent Passerini reaction, and enzymatic kinetic resolution of formed α-acyloxy carboxamides. The presented studies are promising in exploratory proof-of-concept of enzyme-controlled stereodivergent cascade to form an important class of chiral compounds for medicinal chemistry.
Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates
Guo, Qihang,Ren, Xiang,Lu, Zhan
supporting information, p. 880 - 884 (2019/05/16)
Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.
Selective hydrogenation of α,β-unsaturated carbonyl compounds on silica-supported copper nanoparticles
Mendes-Burak, Jorge,Ghaffari, Behnaz,Copéret, Christophe
supporting information, p. 179 - 181 (2019/01/04)
Silica-supported copper nanoparticles prepared via surface organometallic chemistry are highly efficient for the selective hydrogenation of various α,β-unsaturated carbonyl compounds yielding the corresponding saturated esters, ketones, and aldehydes in the absence of additives. High conversions and selectivities (>99%) are obtained for most substrates upon hydrogenation at 100-150 °C and under 25 bar of H2.
Electrochemical Hydrogenation with Gaseous Ammonia
Li, Jin,He, Lingfeng,Liu, Xu,Cheng, Xu,Li, Guigen
supporting information, p. 1759 - 1763 (2019/01/16)
As a carbon-free and sustainable fuel, ammonia serves as high-energy-density hydrogen-storage material. It is important to develop new reactions able to utilize ammonia as a hydrogen source directly. Herein, we report an electrochemical hydrogenation of alkenes, alkynes, and ketones using ammonia as the hydrogen source and carbon electrodes. A variety of heterocycles and functional groups, including for example sulfide, benzyl, benzyl carbamate, and allyl carbamate were well tolerated. Fast stepwise electron transfer and proton transfer processes were proposed to account for the transformation.
Pyrrolidine-Based P,O Ligands from Carbohydrates: Easily Accessible and Modular Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Olefins
Elías-Rodríguez, Pilar,Borràs, Carlota,Carmona, Ana T.,Faiges, Jorge,Robina, Inmaculada,Pàmies, Oscar,Diéguez, Montserrat
, p. 5414 - 5424 (2018/12/11)
The potential of P,O-iminosugar based ligands in the Ir-catalyzed asymmetric hydrogenation of minimally functionalized olefins is presented. These new ligands were prepared from easily available carbohydrates (D-mannose, D-ribose and D-arabinose). The stereochemical and polyfunctional diversity of carbohydrates allowed the modulation of the ligands, both from their electronic properties and the rigidity of their backbone. High enantioselectivities (ee’s up to 99 %) can be reached in the hydrogenation of selected tri- and disubstituted substrates.
Preparation method for indanone compound
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Paragraph 0087-0089, (2018/08/28)
The invention especially relates to a preparation method for an indanone compound, belonging to the field of organic synthesis. The preparation method for the indanone compounds comprises the following steps: 1) subjecting a compound as shown in a formula I and a compound as shown in a formula II to a condensation reaction so as to prepare a compound as shown in a formula III; 2) subjecting the compound as shown in the formula III to hydrolysis in the presence of alkali so as to prepare a compound as shown in a formula IV; and 3) carrying out acylation and ring closure on the compound as shownin the formula IV so as to prepare the as shown in a formula V. Compared with the prior art, the preparation method for the indanone compound in the invention has the advantages of low raw material cost, simple operation, low production of waste water, waste gas and industrial residues, high yield and the like, and is more suitable for industrial production; and compared with various traditionalpreparation methods for the indanone compound, the preparation method of the invention has obvious advantages and shows good industrialization prospects.
Synthesis and activity of putative small-molecule inhibitors of the F-box protein SKP2
Shouksmith, Andrew E.,Evans, Laura E.,Tweddle, Deborah A.,Miller, Duncan C.,Willmore, Elaine,Newell, David R.,Golding, Bernard T.,Griffin, Roger J.
, p. 660 - 679 (2015/04/27)
The tetrahydropyran 4-(((3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline was reported to disrupt the SCFSKP2 E3 ligase complex. Efficient syntheses of this tetrahydropyran derivative and analogues, including the des-dimethyl derivative 4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline, are described. The enantiomers of the des-dimethyl compound were obtained using Evans' chiral auxiliaries. Structure-activity relationships for these tetrahydropyrans and analogues have been determined by measurement of growth-inhibitory activities in HeLa cells, which indicated a non-specific mechanism of action that correlates with inhibitor lipophilicity. However, preliminary data with (R)-and (S)-4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline showed enantioselective inhibition of the degradation of p27 in a cell-based assay that acts as a reporter of SKP2 activity.
An improved solvent-free system for the microwave-assisted decarboxylation of malonate derivatives based on the use of imidazole
Tellitu, Imanol,Beitia, Itziar,Díaz, Marta,Alonso, Argi?e,Moreno, Isabel,Domínguez, Esther
, p. 8251 - 8255 (2015/10/05)
A comparative study of the thermal and microwave-assisted decarboxylation of a series of mono- and disubstituted monohydrolyzed malonate derivatives has been carried out. It has been found out that in both circumstances the use of imidazole has a profound effect on the success of the reaction. In general terms the assistance of microwave irradiation accelerates the decarboxylation process significantly and, at the same time, permits the use of minored temperatures with respect to the thermal via. It has been also found that both the thermal and the microwave-assisted transformation can be developed under solvent-free conditions.
Iridium catalysts with Chiral bicyclic pyridine-phosphane ligands for the asymmetric hydrogenation of olefins
Quan, Xu,Parihar, Vijay Singh,Bera, Milan,Andersson, Pher G.
, p. 140 - 146 (2014/01/06)
New bicyclic pyridine-phosphane ligands were prepared, and their iridium complexes were evaluated in asymmetric hydrogenation of trisubstituted olefins with non-coordinating and weakly coordinating substituents. The iridium catalysts showed high reactivity and enantioselectivity for both types of olefins. New pyridine-derived N,P-chelated iridium catalysts were prepared and evaluated in the asymmetric hydrogenation of trisubstituted olefins. High conversions and enantioselectivities were obtained. Copyright
Influence of the position of the substituent on the efficiency of lipase-mediated resolutions of 3-aryl alkanoic acids
Deasy, Rebecca E.,Moody, Thomas S.,Maguire, Anita R.
, p. 1480 - 1487 (2013/12/04)
Hydrolase-catalysed kinetic resolutions to provide enantioenriched α-substituted 3-aryl alkanoic acids are described. (S)-2-Methyl-3- phenylpropanoic acid (S)-1a was prepared in 96% ee by Pseudomonas fluorescens catalysed ester hydrolysis, while, Candida antarctica lipase B (immob) resolved the α-ethyl substituted 3-arylalkanoic acid (R)-1b in 82% ee. The influence of the position of the substituent relative to the ester site on the efficiency and enantioselectivity of the biotransformation is also explored; the same lipases were found to resolve both the α- and β-substituted alkanoic acids. Furthermore, the steric effect of substituents at the C2 stereogenic centre relative to that for their C3 substituted counterparts on the efficiency and stereoselectivity is discussed.
