chiral-phosphine-ligands| Page 25 of 630 | Chiral phosphine ligands

Czako, Barbara’s team published research in Journal of Medicinal Chemistry in 64 | CAS: 2055761-19-6

Journal of Medicinal Chemistry published new progress about 2055761-19-6. 2055761-19-6 belongs to chiral-phosphine-ligands, auxiliary class Spiro[4.5], name is (3S,4S)-3-Methyl-2-oxa-8-azaspiro[4.5]decan-4-amine dihydrochloride, and the molecular formula is C9H20Cl2N2O, Application In Synthesis of 2055761-19-6.

Czako, Barbara published the artcileDiscovery of 6-[(3S,4S)-4-Amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-3-(2,3-dichlorophenyl)-2-methyl-3,4-dihydropyrimidin-4-one (IACS-15414), a Potent and Orally Bioavailable SHP2 Inhibitor, Application In Synthesis of 2055761-19-6, the publication is Journal of Medicinal Chemistry (2021), 64(20), 15141-15169, database is CAplus and MEDLINE.

Src homol. 2 (SH2) domain-containing phosphatase 2 (SHP2) plays a role in receptor tyrosine kinase (RTK), neurofibromin-1 (NF-1), and Kirsten rat sarcoma virus (KRAS) mutant-driven cancers, as well as in RTK-mediated resistance, making the identification of small-mol. therapeutics that interfere with its function of high interest. Our quest to identify potent, orally bioavailable, and safe SHP2 inhibitors led to the discovery of a promising series of pyrazolopyrimidinones that displayed excellent potency but had a suboptimal in vivo pharmacokinetic (PK) profile. Hypothesis-driven scaffold optimization led us to a series of pyrazolopyrazines with excellent PK properties across species but a narrow human Ether-á-go-go-Related Gene (hERG) window. Subsequent optimization of properties led to the discovery of the pyrimidinone series, in which multiple members possessed excellent potency, optimal in vivo PK across species, and no off-target activities including no hERG liability up to 100μM. Importantly, compound 30 (IACS-15414) potently suppressed the mitogen-activated protein kinase (MAPK) pathway signaling and tumor growth in RTK-activated and KRAS^mut xenograft models in vivo.

Referemce:
https://en.wikipedia.org/wiki/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

Liang, Kangjiang’s team published research in Journal of Organic Chemistry in 83 | CAS: 929294-27-9

Journal of Organic Chemistry published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C50H65O4P, Category: chiral-phosphine-ligands.

Liang, Kangjiang published the artcileEnantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides, Category: chiral-phosphine-ligands, the publication is Journal of Organic Chemistry (2018), 83(18), 10948-10958, database is CAplus and MEDLINE.

Nitroxides can absorb both UV and visible light, and their electron can be excited from the π-bonding orbital to the antibonding π* orbital or the n-bonding orbital to the antibonding π* orbital, resp. Despite the reported UV-induced hydrogen atom transfer (HAT) process, the potential of nitroxides for visible light-excited photosynthesis is underexplored. Here we demonstrate that nitroxide can convert indole to its radical through a visible light-induced HAT process. A chiral phosphoric acid-catalyzed cyclization of the in situ-formed imine radical, followed by trapping by another mol. of nitroxide, provides the product in high yield and enantioselectivity. To highlight the novelty and efficiency of this strategy, an asym. total synthesis of natural product (-)-verrupyrroloindoline was accomplished in 5 steps.

Wu, Haibo’s team published research in Journal of Separation Science in 37 | CAS: 297752-25-1

Journal of Separation Science published new progress about 297752-25-1. 297752-25-1 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, and the molecular formula is C15H24O2, Computed Properties of 297752-25-1.

Wu, Haibo published the artcileNovel chiral stationary phases based on peptoid combining a quinine/quinidine moiety through a C9-position carbamate group, Computed Properties of 297752-25-1, the publication is Journal of Separation Science (2014), 37(8), 934-943, database is CAplus and MEDLINE.

By connecting a quinine or quinidine moiety to the peptoid chain through the C9-position carbamate group, the authors synthesized two new chiral selectors. After immobilizing them onto 3-mercaptopropyl-modified silica gel, two novel chiral stationary phases were prepared With neutral, acid, and basic chiral compounds as analytes, the authors evaluated these two stationary phases and compared their chromatog. performance with chiral columns based on quinine tert-Bu carbamate and the previous peptoid. From the resolution of neutral and basic analytes under normal-phase mode, the new stationary phases exhibited much better enantioselectivity than the quinine tert-Bu carbamate column; the peptoid moiety played an important role in enantiorecognition, which controlled the elution orders of enantiomers; the assisting role of the cinchona alkaloid moieties was observed in some separations Under acid polar organic phase mode, cinchona alkaloid moieties introduced excellent enantiorecognitions for chiral acid compounds; in some separations, the peptoid moiety affected enantioseparations as well. Overall, chiral moieties with specific enantioselectivity improve the performance of peptoid chiral stationary phase efficiently.

Wu, Zijun’s team published research in ACS Catalysis in 7 | CAS: 297752-25-1

ACS Catalysis published new progress about 297752-25-1. 297752-25-1 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, and the molecular formula is C5H10Cl3O3P, Safety of (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide.

Wu, Zijun published the artcileEnantioselective Medium-Ring Lactone Synthesis through an NHC-Catalyzed Intramolecular Desymmetrization of Prochiral 1,3-Diols, Safety of (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, the publication is ACS Catalysis (2017), 7(11), 7647-7652, database is CAplus.

A highly enantioselective intramol. annulation reaction of 1,3-diols catalyzed by a triazolium N-heterocyclic carbene (NHC) precatalyst is disclosed, affording the corresponding medium-sized lactones in moderate to good yields with high enantioselectivities. It is worth noting that this compatible catalytic system was successfully applied to assemble a broad range of chiral medium-sized lactones, including ones with eight-, nine-, ten-, eleven-, and twelve-membered rings.

Zhang, Hua’s team published research in ACS Catalysis in 12 | CAS: 929294-27-9

ACS Catalysis published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C20H21ClN4O4, Category: chiral-phosphine-ligands.

Zhang, Hua published the artcileVisible-Light-Mediated Formal Carbene Insertion Reaction: Enantioselective Synthesis of 1,4-Dicarbonyl Compounds Containing All-Carbon Quaternary Stereocenter, Category: chiral-phosphine-ligands, the publication is ACS Catalysis (2022), 12(9), 5510-5516, database is CAplus.

Authors developed an efficient visible-light-mediated formal carbene insertion reaction of 1,3-diketones with diazoesters for the construction of enantioenriched 1,4-dicarbonyl compounds with a quaternary carbon center. Combining visible light and a Bronsted acid catalyst, chiral 1,4-dicarbonyl compounds were achieved in good yields with high enantioselectivities by a photochem. carbene transfer protocol.

Yang, Xiangbo’s team published research in European Journal of Medicinal Chemistry in 218 | CAS: 2055761-19-6

European Journal of Medicinal Chemistry published new progress about 2055761-19-6. 2055761-19-6 belongs to chiral-phosphine-ligands, auxiliary class Spiro[4.5], name is (3S,4S)-3-Methyl-2-oxa-8-azaspiro[4.5]decan-4-amine dihydrochloride, and the molecular formula is C16H24BF4Ir, Product Details of C9H20Cl2N2O.

Yang, Xiangbo published the artcileDiscovery of thalidomide-based PROTAC small molecules as the highly efficient SHP2 degraders, Product Details of C9H20Cl2N2O, the publication is European Journal of Medicinal Chemistry (2021), 113341, database is CAplus and MEDLINE.

Design, synthesis and evaluation of a series of thalidomide-based heterobifunctional mols. and identified compound I as highly efficient SHP2 degrader with a DC₅₀ of 6.02 nM was described. Further mechanism investigation illustrated that compound I came into function through targeted SHP2 protein degradation

Zhao, Jianchao’s team published research in Journal of Separation Science in 38 | CAS: 297752-25-1

Zhao, Jianchao published the artcileImprovement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification, Recommanded Product: (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, the publication is Journal of Separation Science (2015), 38(22), 3884-3890, database is CAplus and MEDLINE.

To improve the chiral recognition capability of a cinchona alkaloid crown ether chiral stationary phase, the crown ether moiety was modified by the chiral group of (1S,2S)-2-aminocyclohexyl phenylcarbamate. Both quinine and quinidine-based stationary phases were evaluated by chiral acids, chiral primary amines and amino acids. The quinine/quinidine and crown ether provided ion-exchange sites and complex interaction site for carboxyl group and primary amine group in amino acids, resp., which were necessary for the chiral discrimination of amino acid enantiomers. The introduction of the chiral group greatly improved the chiral recognition for chiral primary amines. The structure of crown ether moiety was proved to play a dominant role in the chiral recognitions for chiral primary amines and amino acids.

Yang, Chen’s team published research in Journal of Organic Chemistry in 78 | CAS: 297752-25-1

Journal of Organic Chemistry published new progress about 297752-25-1. 297752-25-1 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, and the molecular formula is C4H5F3N2O3S, Recommanded Product: (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide.

Yang, Chen published the artcileTheoretical Study on the Acidities of Chiral Phosphoric Acids in Dimethyl Sulfoxide: Hints for Organocatalysis, Recommanded Product: (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, the publication is Journal of Organic Chemistry (2013), 78(14), 7076-7085, database is CAplus and MEDLINE.

The pK_a values of 41 chiral phosphoric acid-family catalysts in DMSO were predicted using the SMD/M06-2x/6-311++G(2df,2p)//B3LYP/6-31+G(d) method for the first time. The study showed that the calculated pK_a‘s range from -4.23 to 6.16 for absolute pK_a values and from -4.21 to 6.38 for relative pK_a values. Excellent agreement between the calculated and exptl. pK_a‘s was achieved for the few available cases (to a precision of around 0.4 pK_a unit), indicating that this strategy may be suitable for calculating highly accurate pK_a‘s. A good linear correlation between the pK_a‘s for 3 and 3’ disubstituted Ph BINOL phosphoric acids and the Hammett constants was obtained. The relationship between the acidities of phosphoric acid catalysts and their reaction activity and selectivity was also discussed. Knowledge of the pK_a values of phosphoric acids should be of great value for the understanding of chiral Bronsted acid-catalyzed reactions and may aid in future catalyst design.

Wang, Cheng-Jie’s team published research in Organic Chemistry Frontiers in 7 | CAS: 929294-27-9

Organic Chemistry Frontiers published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C3H5BN2O2, Recommanded Product: R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate.

Wang, Cheng-Jie published the artcileCatalytic asymmetric 1,4-type Friedel-Crafts (hetero)arylations of 1-azadienes: the highly enantioselective syntheses of chiral hetero-triarylmethanes, Recommanded Product: R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, the publication is Organic Chemistry Frontiers (2020), 7(3), 609-616, database is CAplus.

Direct enantioselective Michael-type Friedel-Crafts arylations and heteroarylations of s-cis 1-azadienes I (R = H, Me; R¹ = Ph, thiophen-2-yl, 4-chlorophenyl, etc.) were achieved by applying chiral bifunctional tertiary amine-urea catalysts when using 2-naphthols II (R² = H, 6-(naphthalen-1-yl), 7-methoxy, 6-bromo) as the nucleophiles, and phosphoric acid catalysts when using indoles III (R³ = H, Me; R⁴ = H, Me, Ph; R⁵ = H, OMe, Br) as the nucleophiles. These two catalytic protocols efficiently enabled access to a diverse variety of important benzofuran-containing hetero-triarylmethanes IV and V in up to 98% yield and with 99.5 : 0.5 er.

Xu, Qi’s team published research in Organic Letters in 24 | CAS: 1365531-76-5

Organic Letters published new progress about 1365531-76-5. 1365531-76-5 belongs to chiral-phosphine-ligands, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (S)-2,2′-Bis(diphenylphosphino)-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl, and the molecular formula is C11H14O2, Formula: C40H36O4P2.

Xu, Qi published the artcileCu(I)-Catalyzed Asymmetric Arylation of Pyrroles with Diaryliodonium Salts toward the Synthesis of N-N Atropisomers, Formula: C40H36O4P2, the publication is Organic Letters (2022), 24(17), 3138-3143, database is CAplus and MEDLINE.

The copper(I) catalysis using a bis(phosphine) dioxide ligand could catalyze the desym. C-H arylation of prochiral bipyrroles was reported. More than 50 nitrogen-nitrogen atropisomers I [R¹ = Ph, 3-ClC₆H₄, 2-naphthyl, etc.; R² = Me, Et, Bn, etc.; R³ = Me, Et, i-Pr; R⁴ = H, Me; R¹R⁴ = CH=CH-CH=CH; Ar = Ph, 4-MeC₆H₄, 3-ClC₆H₄, etc.] were achieved in good to excellent yields with excellent enantioselectivities (≤97% yield, ≤98% ee). The reaction proceeded under mild conditions with good functional group compatibility on arenes and diaryliodonium salts. Moreover, this principle enabled iterative arylation of the bipyrroles to enantioselectively arylate different positions during the catalysis of copper.