65838-10-0Relevant articles and documents
Machine-Assisted Preparation of a Chiral Diamine Ligand Library and In Silico Screening Using Ab Initio Structural Parameters for Heterogeneous Chiral Catalysts
Kobayashi, Shū,Kuremoto, Tatsuya,Sadatsune, Ren,Yamashita, Yasuhiro,Yasukawa, Tomohiro
supporting information, p. 4204 - 4208 (2021/08/09)
A ligand library containing 31 chiral diamines was synthesized using a flow-based semiautomatic reductive amination system. These ligands were evaluated in a continuous-flow asymmetric 1,4-addition reaction with a heterogeneous Ni catalyst. Based on the experimental results of ab initio DFT calculations, a prediction model for enantioselectivities was successfully constructed. Furthermore, virtual screening of possible ligands was conducted to identify promising structures, which showed good enantioselectivities in experiments. (Figure presented.).
Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides
Devannah, Vijayarajan,Sharma, Rajgopal,Watson, Donald A.
supporting information, p. 8436 - 8440 (2019/06/13)
A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched products with nitrogen-bearing fully substituted carbon centers.
Nitroalkenes in the Ni(II) Catalyzed Asymmetric Michael Addition. Convenient Route to the Key Intermediate of Brivaracetam
Reznikov, Alexander N.,Kapranov, Leonid E.,Ivankina, Valentina V.,Sibiryakova, Anastasiya E.,Rybakov, Victor B.,Klimochkin, Yuri N.
, (2018/11/27)
A series of Ni(II) complexes with novel chiral ligands derived from (1R,2R)-1,2-diphenylethane-1,2-diamine was synthesized. The catalytic activity of these complexes in the asymmetric Michael reaction is demonstrated. Asymmetric addition of diethyl malonate to ω-nitrostyrene and 1-nitropent-1-ene in the presence of these complexes leads to the enantiomerically enriched diethyl (S)-2-(2-nitro-1-phenylethyl)malonate (up to 96 % ee) and (R)-diethyl 2-(1-nitropenthan-2-yl)malonate (up to 91 % ee). (4R)-4-Propylpyrrolidin-2-one, the key intermediate of antiepileptic drug brivaracetam, was obtained from the corresponding nitroester.
Synthesis and crystal structure of a chiral lactam and three amino alcohols as potential protein tyrosine phosphates 1B inhibitors
?zhan Kocakaya, ?afak,Karakaplan, Mehmet,Scopelliti, Rosario
, p. 1342 - 1349 (2017/10/13)
Chiral lactam 2 and three chiral β-amino alcohols 3–5 have been synthesized and characterized by spectroscopic techniques. Regioselective ring opening reaction of chiral styrene oxide by an amine nucleophile was confirmed by X-ray diffraction data. Ligand 2–4 crystallizes in the tetragonal, orthorhombic and tetragonal crystal lattice system respectively. Ligands 2–6 have been used as potential inhibitors for protein tyrosine phosphatase 1B enzyme (PTP1B). The potential inhibitor effect of these molecules to the target protein was investigated by Dock and molecular dynamics calculations. Dock score analysis and Lipinski parameters suggested that ligands 1, 2, 4–6 are potential inhibitors towards PTP1B, thus indicating that the residues Arg24, Arg254 and Met258, Asp29 in the second active site of PTP1B are essential for the high selectivity of inhibitors. The results indicate that the polar hydrogen bonding interacts with Asp29, Gln102, and the amino acid residues of PTP1B are responsible for governing inhibitory potency of ligands 1–6.
Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols
Tsygankov, Alexey A.,Chun, Man-Seog,Samoylova, Alexandra D.,Kwon, Seongyeon,Kreschenova, Yuliya M.,Kim, Suhyeon,Shin, Euijin,Oh, Jinho,Strelkova, Tatyana V.,Kolesov, Valerii S.,Zubkov, Fedor I.,Semenov, Sergei E.,Fedyanin, Ivan V.,Chusov, Denis
supporting information, p. 615 - 619 (2017/03/11)
A series of N,N′-dialkylated derivatives of (1R,2R)-cyclohexane-1,2-diamine were synthesized, and a new approach to the one-pot preparation of this type of amine was demonstrated. The prepared diamines were used as organocatalysts for the two-step synthesis of α-hydroxy γ-keto esters from arenes, chlorooxoacetates, and ketones; they were also used as chiral ligands for Meervein-Ponndorf-Verley reductions and Henry reactions.
Mechanosynthesis of Second-Sphere Coordination Salts and Chelating Complexes: Structures, Reversible Transformations, and Nitroaromatic Explosives Sensing
Li, Hai-Tao,Duan, Wen-Long,Guo, Fang
, p. 4750 - 4756 (2017/10/24)
We have investigated the mechanosynthesis of a series of second-sphere salts, guest?[H2L]2+·[MCl4]2– [L = N,N′-dibenzyl-(±)-trans-1,2-diaminocyclohexane], and the reversible transformations to their chelating coordination complexes [MCl2(L)] through dehydrochlorination reactions. The second-sphere salts and their corresponding coordination complexes show different solid-state fluorescence spectra. The complex ZnCl2(L) (2′) acts as a sensor for the highly sensitive detection of nitroaromatic compounds through fluorescence quenching.
Gas-Solid Chemisorption/Adsorption and Mechanochemical Selectivity in Dynamic Nonporous Hybrid Metal Organic Materials
Li, Haitao,Guo, Fang,Kou, Meng,Famulari, Antonino,Fu, Qiang,Marti-Rujas, Javier
supporting information, p. 6584 - 6590 (2017/06/13)
Gas-solid chemisorption of HCl and adsorption of MeOH/EtOH by nonporous chiral copper(II) coordination complexes 1·MeOH and 1·MeOH occur in a cooperative and dynamic manner to give solvated second sphere adducts 1′·MeOH/EtOH. The chemisorption process involves dramatic atomic rearrangements in the crystalline state upon cleavage and formation of H-Cl, N-H, Cu-N, and Cu-Cl coordination and covalent bonds from the gas and solid state, respectively. Using mechanochemistry, the chloride-bridged coordination complex 1·MeOH is selectively produced by means of a dehydrochlorination reaction, but not in solution in which a mixture of 1·MeOH and 1·MeOH is obtained. 1·MeOH also via chemisorption and adsorption can trap HCl and MeOH to give the second sphere adduct 1′·MeOH. The adsorption process is confirmed by forming the second sphere adduct 1′·EtOH by exposing both 1·MeOH and 1·MeOH to HCl and ethanol. Quantum-mechanical (QM) calculations specific for solid phases give insights into the relative stabilities of the hybrid metal organic materials involved in the mechanochemical reaction producing selectively 1·MeOH, giving a good agreement with the experimental results.
Preparations of Saturated N-P-N Type Secondary Phosphine Oxides and their Applications in Cross-Coupling Reactions
Chang, Yu-Chang,Liang, Ya-Han,Hong, Fung-E
, p. 353 - 367 (2016/05/09)
A series of cyclohexane-1,2-diamine (3a-3d) and benzene-1,2-diamine derivatives (3e-3h) were pre- pared. Followed by hydrolysis, the reaction of 3a-3c with PCl3 successfully led to the formation of cor- responding metastable saturated heteroato
Synthesis and application of amino alcohol imides as NMR solvating agents for chiral discrimination of carboxylic acids
Karakaplan, Mehmet,Jameel, Basam
, p. 597 - 602 (2016/07/11)
A series of amino alcohol imides 2–8 have been synthesized from commercially available starting materials by regioselective ring opening reaction of epoxides with chiral amines. Compounds 2–8 were tested as chiral solvating agents (CSAs) for enantiomeric discrimination of biological important carboxylic acids. C2-Symmetric (S,R,R,S)-3 was found to be a satisfactory CSA for mandelic acid with ΔΔδ of 24.8?Hz. CSA (S,S)-5 exhibited the best enantiomeric discrimination for α-phenyl-α-methoxyacetic acid with ΔΔδ of 32?Hz. Enantiomeric differentiated values found for mandelic acid, o-chloro mandelic acid, ibuprofen and naproxen are 7.2, 4.4, 2 and 3?Hz respectively.
H2 CHX dedpa and H4 CHX octapa-Chiral acyclic chelating ligands for 67/68Ga and 111In radiopharmaceuticals
Ramogida, Caterina F.,Cawthray, Jacqueline F.,Boros, Eszter,Ferreira, Cara L.,Patrick, Brian O.,Adam, Michael J.,Orvig, Chris
, p. 2017 - 2031 (2015/06/09)
The chiral acyclic ligands H2CHXdedpa (N4O2), H2CHXdedpa-bb (N4O2), and H4CHXoctapa (N4O4) (CHX = cyclohexyl/cyclohexane, H2dedpa = 1,2-[[6-carbo