34469-09-5Relevant articles and documents
An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones
Huo, Shangfei,Wang, Qingwei,Zuo, Weiwei
supporting information, p. 7959 - 7967 (2020/06/26)
We report the design of a new iron catalyst for the asymmetric transfer hydrogenation of ketones. This type of iron catalyst combines the structural characteristics of the Noyori hydrogenation catalyst (an axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl fragment and the metal-ligand bifunctional motif) and an ene(amido) group that can activate the iron center. After activation by 8 equivalents of potassiumtert-butoxide, (SA,RP,SS)-7aand (SA,RP,SS)-7bare active but nonenantioselective catalysts for the transfer hydrogenation of acetophenone and α,β-unsaturated aldehydes at room temperature in isopropanol. A maximum turnover number of 14480 was observed for (SA,RP,SS)-7ain the reduction of acetophenone. The right combination of the stereochemistry of the axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl group and the carbon-centered chiral amine-imine moiety in (SA,RP,RR)-7b′afforded an enantioselective catalyst for the preparation of chiral alcohols with moderate to good yields and a broad functional group tolerance.
AMIDO THIADIAZOLE DERIVATIVES AS NADPH OXIDASE INHIBITORS
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Page/Page column 83; 84, (2016/07/05)
The present invention is related to amino thiazole derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).
waylen apperception HIV reverse transcriptase inhibitors in accordance with the law of the process for the asymmetric synthesis of one-pot synthesis (by machine translation)
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Paragraph 0179; 0180; 0181, (2016/10/07)
The invention relates to a novel one pot method asymmetric synthesis process of a (S)-6-chlorine-4-cylopropyl ethylnen-4-trifluoromethyl-1,4-dihydro-2H-1,3-benzoxazine-2-ketone (Efavirenz) compound, the compound can be used as an reverse transcriptase inhibitor for human immunodeficiency virus (HIV). The invention also relates to a novel aminoalcohol ligand used for the process.
Theoretical and Experimental Optimization of a New Amino Phosphite Ligand Library for Asymmetric Palladium-Catalyzed Allylic Substitution
Magre, Marc,Biosca, Maria,Norrby, Per-Ola,Pàmies, Oscar,Diéguez, Montserrat
, p. 4091 - 4107 (2015/12/26)
A new library of modular amino phosphite ligands obtained in a few synthetic steps from enantiopure amino alcohols has been tested in asymmetric Pd-catalyzed allylic substitution. The modular ligand design is crucial to find highly selective catalysts for each substrate type using a wide range of C-, N-, and O-nucleophiles. A DFT study of the species responsible for the enantiocontrol was used to optimize the ligand structure. By selecting the ligand components, we were able to identify unprecedented catalytic systems that can create new chiral C-C, C-N, and C-O bonds in a variety of substrate types (hindered and unhindered) in high yields and enantioselectivities (ee values up to 99 %). Further studies on the Pd-π-allyl intermediates provided a deep understanding of the effect of ligand structure in the origin of enantioselectivity. Potential applications of the new Pd/amino phosphite catalysts were demonstrated by the practical synthesis of a range of chiral carbocycles by simple tandem reactions, with no loss of enantioselectivity.
Discovery of pyrroloaminopyrazoles as novel PAK inhibitors
Guo, Chuangxing,McAlpine, Indrawan,Zhang, Junhu,Knighton, Daniel D.,Kephart, Susan,Johnson, M. Catherine,Li, Haitao,Bouzida, Djamal,Yang, Anle,Dong, Liming,Marakovits, Joseph,Tikhe, Jayashree,Richardson, Paul,Guo, Lisa C.,Kania, Robert,Edwards, Martin P.,Kraynov, Eugenia,Christensen, James,Piraino, Joseph,Lee, Joseph,Dagostino, Eleanor,Del-Carmen, Christine,Deng, Ya-Li,Smeal, Tod,Murray, Brion W.
experimental part, p. 4728 - 4739 (2012/07/28)
The P21-activated kinases (PAK) are emerging antitumor therapeutic targets. In this paper, we describe the discovery of potent PAK inhibitors guided by structure-based drug design. In addition, the efflux of the pyrrolopyrazole series was effectively reduced by applying multiple medicinal chemistry strategies, leading to a series of PAK inhibitors that are orally active in inhibiting tumor growth in vivo.
Enantioselective reduction of α-substituted ketones mediated by the boronate ester TarB-NO2
Eagon, Scott,Ball-Jones, Nicholas,Haddenham, Dustin,Saavedra, Jaime,Delieto, Cassandra,Buckman, Matthew,Singaram, Bakthan
supporting information; scheme or table, p. 6418 - 6421 (2010/12/30)
A facile and mild reduction procedure is reported for the preparation of chiral secondary alcohols prepared from α-substituted ketones using sodium borohydride and the chiral boronate ester (l)-TarB-NO2. Direct reduction of substituted ketones bearing Lewis basic heteroatoms generally provided secondary alcohols of only modest enantiomeric excess likely due to either competition between the target carbonyl and the functionalized sidechains at the Lewis acidic boron atom in TarB-NO2 or the added steric bulk of the α-sidechain. As an alternative method, these substrates were synthesized using TarB-NO2 via a two-step procedure involving the reduction of an α-halo ketone to a chiral terminal epoxide, followed by regioselective/regiospecific epoxide opening by various nucleophiles. This procedure provides access to a variety of functionalized secondary alcohols including β-hydroxy ethers, thioethers, nitriles, and amines with enantiomeric excesses of 94% and yields up to 98%.
Asymmetric synthesis of β-dialkylamino alcohols by transfer hydrogenation of α-dialkylamino ketones
Kosmalski, Tomasz,Wojtczak, Andrzej,Zaidlewicz, Marek
experimental part, p. 1138 - 1143 (2009/09/27)
Transfer hydrogenation of representative aryl and heteroaryl dialkylaminomethyl ketones with formic acid-triethylamine, catalyzed by RuCl[(R,R)-TsDPEN](η-p-cymene), produces the corresponding β-dialkylamino alcohols, 97-99% ee, in 50-73% yields. Asymmetric synthesis of (R)-macromerine, 98% ee, the cactus Coryphantha macromeris alkaloid, is also described.
CARBONYLAMINO PYRROLOPYRAZOLES, POTENT KINASE INHIBITORS
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Page/Page column 45, (2009/12/28)
Carbonylamino Pyrrolopyrazole compounds of formula I, compositions including these compounds and methods of their use are provided. Preferred compounds of formula I have activity as protein kinase inhibitors, including as inhibitors of PAK4.
Catalytic asymmetric borane reduction of prochiral ketones by using (S)-2-(anilinomethyl)pyrrolidine
Hosoda, Naoya,Iogawa, Yoshihiro,Shimada, Yuichi,Asami, Masatoshi
experimental part, p. 274 - 277 (2009/03/12)
Catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of (S)-2-(anilinornethyl)pyrrolidine. Chiral secondary alcohols were obtained with moderate to high enantiomeric excesses (up to 96% ee).
