October 13, 2022 | Page 2 of 10 | Chiral phosphine ligands

Tanaka, Ken’s team published research in Synlett in 2008-07-01 | 139139-93-8

Synlett published new progress about Alkadiynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Electric Literature of 139139-93-8.

Tanaka, Ken; Takahashi, Yoshihiro; Suda, Takeshi; Hirano, Masao published the artcile< Synthesis of enantioenriched N-aryl-2-pyridones with chiral C-N axes by rhodium-catalyzed [2+2+2] cycloaddition of alkynes with isocyanates>, Electric Literature of 139139-93-8, the main research area is alkadiyne phenyl isocyanate stereoselective cycloaddition rhodium catalyst; pyridone stereoselective preparation.

Enantioenriched N-aryl-2-pyridones with axially chiral C-N bonds were prepared by a cationic rhodium(I)-BINAP or tol-BINAP-catalyzed enantioselective [2+2+2] cycloaddition of alkadiynes with ortho-substituted Ph isocyanates.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Tsuchikama, Kyoji’s team published research in Synlett in 2007-06-01 | 139139-93-8

Tsuchikama, Kyoji; Yoshinami, Yusuke; Shibata, Takanori published the artcile< Rhodium-complex-catalyzed [2+2+2] cycloaddition of diynes and carbonyl compounds>, Product Details of C44H40P2, the main research area is diyne carbonyl stereoselective cycloaddition rhodium BINAP catalyst; hydropyran stereoselective preparation electrocyclic ring opening; cyclopentene stereoselective preparation; hydropyrrole stereoselective preparation; hydrofuran stereoselective preparation.

A Rh-BINAP complex was used to catalyze the hetero-[2+2+2] cycloaddition of sym. 1,6-diynes and carbonyl moiety of keto esters, a diketone, and an aldehyde to give bicyclic α-pyrans, which were readily transformed into monocyclic compounds via the following electrocyclic ring opening. In the reaction of an unsym. 1,6-diyne and a 1,7-diyne, α-pyrans with a quaternary carbon stereocenter were obtained in moderate to excellent ee using a chiral rhodium catalyst.

Kharlamova, Alisa D’s team published research in Molecules in 2021 | 277306-29-3

Molecules published new progress about Activation energy. 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Related Products of 277306-29-3.

Kharlamova, Alisa D.; Abel, Anton S.; Averin, Alexei D.; Maloshitskaya, Olga A.; Roznyatovskiy, Vitaly A.; Savelyev, Evgenii N.; Orlinson, Boris S.; Novakov, Ivan A.; Beletskaya, Irina P. published the artcile< Mono- and diamination of 4,6-dichloropyrimidine, 2,6-dichloropyrazine and 1,3-dichloroisoquinoline with adamantane-containing amines>, Related Products of 277306-29-3, the main research area is heteroaryl substituted adamantane containing amine preparation; dichloropyrimidine dichloropyrazine dichloroisoquinoline adamantane containing amine amination palladium catalyst; Pd catalysis; adamantane; amination; amines; isoquinoline; pyrazine; pyrimidine.

N-heteroaryl substituted adamantane-containing amines, e.g., I were of substantial interest for their perspective antiviral and psychotherapeutic activities. Chlorine atom at alpha-position of N-heterocycles was substituted by amino group using convenient nucleophilic substitution reactions with a series of adamantylalkylamines. The prototropic equilibrium in these compounds was studied using NMR spectroscopy. The introduction of second amino substituent in 4-amino-6-chloropyrimidine, 2-amino-chloropyrazine and 1-amino-3-chloroisoquinoline was achieved using Pd(0) catalysis.

Molecules published new progress about Activation energy. 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Related Products of 277306-29-3.

Ward, Richard A’s team published research in Journal of Medicinal Chemistry in 2012-04-12 | 606-68-8

Journal of Medicinal Chemistry published new progress about Antitumor agents. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Electric Literature of 606-68-8.

Ward, Richard A.; Brassington, Claire; Breeze, Alexander L.; Caputo, Alessandro; Critchlow, Susan; Davies, Gareth; Goodwin, Louise; Hassall, Giles; Greenwood, Ryan; Holdgate, Geoffrey A.; Mrosek, Michael; Norman, Richard A.; Pearson, Stuart; Tart, Jonathan; Tucker, Julie A.; Vogtherr, Martin; Whittaker, David; Wingfield, Jonathan; Winter, Jon; Hudson, Kevin published the artcile< Design and Synthesis of Novel Lactate Dehydrogenase A Inhibitors by Fragment-Based Lead Generation>, Electric Literature of 606-68-8, the main research area is lactate dehydrogenase A inhibitor preparation lead generation SAR.

Lactate dehydrogenase A (LDHA) catalyzes the conversion of pyruvate to lactate, utilizing NADH as a cofactor. It has been identified as a potential therapeutic target in the area of cancer metabolism In this manuscript we report our progress using fragment-based lead generation (FBLG), assisted by x-ray crystallog. to develop small mol. LDHA inhibitors. Fragment hits were identified through NMR and SPR screening and optimized into lead compounds with nanomolar binding affinities via fragment linking. Also reported is their modification into cellular active compounds suitable for target validation work.

Tsui, Gavin C’s team published research in Angewandte Chemie, International Edition in 2012 | 277306-29-3

Angewandte Chemie, International Edition published new progress about Bicyclic compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Application of C32H40FeP2.

Tsui, Gavin C.; Lautens, Mark published the artcile< Rhodium(I)-Catalyzed Domino Asymmetric Ring Opening/Enantioselective Isomerization of Oxabicyclic Alkenes with Water>, Application of C32H40FeP2, the main research area is rhodium catalyzed domino asym ring opening isomerization oxabicycloalkene water; hydroxytetralone enantioselective preparation.

Enantio-enriched 2-hydroxy-1-tetralones are formed from oxabicyclic alkenes through a novel RhI-catalyzed domino reaction. The proposed mechanism involves water-induced asym. ring opening to generate chiral trans-1,2-diol intermediates and subsequent enantioselective isomerization (I → II → III).

Pradal, Alexandre’s team published research in Tetrahedron in 2011 | 325168-88-5

Tetrahedron published new progress about Addition reaction catalysts, stereoselective. 325168-88-5 belongs to class chiral-phosphine-ligands, and the molecular formula is C48H50P2, Name: (S)-(+)-4,12-Bis(di(3,5-xylyl)phosphino)-[2.2]-paracyclophane.

Pradal, Alexandre; Chao, Chung-Meng; Vitale, Maxime R.; Toullec, Patrick Y.; Michelet, Veronique published the artcile< Asymmetric Au-catalyzed domino cyclization/nucleophile addition reactions of enynes in the presence of water, methanol and electron-rich aromatic derivatives>, Name: (S)-(+)-4,12-Bis(di(3,5-xylyl)phosphino)-[2.2]-paracyclophane, the main research area is asym gold catalyst cyclization nucleophilic addition enyne.

An efficient Au(I) catalytic system is described for the asym. domino cyclization/functionalization reactions of functionalized 1,6-enynes in the presence of an external nucleophile. The use of (R)-4-MeO-3,5-(t-Bu)2-MeOBIPHEP ligand associated with gold led to clean rearrangements implying the formal addition of an oxygen or carbon nucleophile to an alkene followed by a cyclization process. The enantiomeric excesses were highly dependent on the substrate/nucleophile combination. Very good enantiomeric excesses up to 98% were obtained in the case of substrates bearing larger groups (hindered diesters and disulfones) and in the case of hindered carbon nucleophiles.

Hirata, Shuzo’s team published research in Journal of Physical Chemistry C in 2020-11-12 | 139139-93-8

Journal of Physical Chemistry C published new progress about Chromophores. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Formula: C44H40P2.

Hirata, Shuzo; Hara, Hyuman; Bhattacharjee, Indranil published the artcile< Phosphorescence Quenching of Heavy-Atom-Free Dopant Chromophores Triggered by Thermally Activated Triplet Exciton Diffusion of a Conjugated Crystalline Host>, Formula: C44H40P2, the main research area is phosphorescence quenching heavy atom dopant chromophore thermally activated triplet.

Persistent room-temperature phosphorescence (pRTP) from aggregated mol. crystalline materials is important for stable high-resolution afterglow imaging. However, an unclear understanding concerning the deactivation mechanism from the lowest triplet excited state (T1) precludes the development of highly efficient pRTP. Here, we report the reasons for the presence and absence of pRTP from a heavy-atom-free conjugated dopant in heavy-atom-free conjugated mol. crystals. N,N-di(9H-fluoren-2-yl)phenanthrene-3-amine (DFAP) was sep. doped into fluorene crystals and (S)-2,2′-bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthalene ((S)-H8-BINAP) crystals. DFAP doped in fluorene crystals with stronger intermol. interactions did not generate RTP, while DFAP doped in (S)-H8-BINAP crystals with weaker intermol. interactions showed strong pRTP. The pRTP of DFAP doped in (S)-H8-BINAP crystals is explained by the deep confinement of the T1 of DFAP in the (S)-H8-BINAP crystals with a large T1 energy. The absence of RTP from DFAP doped in fluorene crystals is explained by the temperature dependence of phosphorescence and quantum calculations, which suggest that deactivation is mainly caused by quenching after diffusion of triplet excitons of the host crystals. The temperature dependence of the triplet-triplet annihilation-based delayed fluorescence of the fluorene crystalline host confirms that the triplet diffusion of the fluorene crystalline host deactivates the triplet excitons of DFAP.

Journal of Physical Chemistry C published new progress about Chromophores. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Formula: C44H40P2.

Loh, Charles C J’s team published research in Angewandte Chemie, International Edition in 2016 | 277306-29-3

Angewandte Chemie, International Edition published new progress about Aliphatic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Synthetic Route of 277306-29-3.

Loh, Charles C. J.; Schmid, Matthias; Webster, Robert; Yen, Andy; Yazdi, Shabnam K.; Franke, Patrick T.; Lautens, Mark published the artcile< Rhodium-Catalyzed Asymmetric Cycloisomerization and Parallel Kinetic Resolution of Racemic Oxabicycles>, Synthetic Route of 277306-29-3, the main research area is racemic oxabicyclic alkene rhodium asym cycloisomerization kinetic resolution catalyst; alkenes; heterocycles; isomerization; kinetic resolution; rhodium.

While desymmetrizations by intermol. asym. ring-opening reactions of oxabicyclic alkenes with various nucleophiles have been reported over the past two decades, the demonstration of an intramol. variant is unknown. Reported herein is the first rhodium-catalyzed asym. cycloisomerization of meso-oxabicyclic alkenes tethered to bridgehead nucleophiles, thus providing access to tricyclic scaffolds through a myriad of enantioselective C-O, C-N, and C-C bond formations. Moreover, we also demonstrate a unique parallel kinetic resolution, whereby racemic oxabicycles bearing two different bridgehead nucleophiles can be resolved enantioselectively.

Brawn, Ryan A’s team published research in Organic Letters in 2013-07-05 | 277306-29-3

Organic Letters published new progress about Enantioselective synthesis. 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Formula: C32H40FeP2.

Brawn, Ryan A.; Guimaraes, Cristiano R. W.; McClure, Kim F.; Liras, Spiros published the artcile< Enantioselective Hydroarylation of Bridged [3.2.1] Heterocycles: An Efficient Entry into the Homoepibatidine Skeleton>, Formula: C32H40FeP2, the main research area is homoepibatidine analog preparation enantioselective hydroarylation.

Achiral [3.2.1] bridged heterocycles containing a bridging amide can undergo enantioselective hydroarylation reactions under rhodium(I) catalysis. These reactions proceed in high yield and enantioselectivity in most cases, under mild reaction conditions and using com. available Josiphos ligands. The phosphine ligand structure and the protecting group on the nitrogen both have significant effects on the selectivity and yield of the reactions. E.g., the homoepibatidine oxa analog I was prepared

Organic Letters published new progress about Enantioselective synthesis. 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Formula: C32H40FeP2.

Nguyen, Qui-Hien’s team published research in Journal of the American Chemical Society in 2020-02-05 | 139139-93-8

Journal of the American Chemical Society published new progress about Arylation catalysts, stereoselective. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Formula: C44H40P2.

Nguyen, Qui-Hien; Guo, Shu-Min; Royal, Titouan; Baudoin, Olivier; Cramer, Nicolai published the artcile< Intermolecular Palladium(0)-Catalyzed Atropo-enantioselective C-H Arylation of Heteroarenes>, Formula: C44H40P2, the main research area is heteroarene azole palladium monooxidized bisphosphine chiral ligand enantioselective arylation; atropisomeric heterobiaryls preparation.

Atropisomeric (hetero)biaryls are motifs with increasing significance in ligands, natural products, and biol. active mols. The straightforward construction of the stereogenic axis by efficient C-H functionalization methods is extremely rare and challenging. An intermol. and highly enantioselective C-H arylation of relevant heteroarenes providing an efficient access to atropisomeric (hetero)biaryls is reported. The use of a Pd(0) complex equipped with H8-BINAPO as a chiral ligand enables the direct functionalization of a broad range of 1,2,3-triazoles and pyrazoles in excellent yields and selectivities of up to 97.5:2.5 er. The method also allows for an atroposelective double C-H arylation for the construction of two stereogenic axes with >99.5:0.5 er.