M.W=350-400| Chiral phosphine ligands

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.

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

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.

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

Wang, Dongqiang published the artcilePreparation and evaluation of novel chiral stationary phases based on quinine derivatives comprising crown ether moieties, Quality Control of 297752-25-1, the publication is Journal of Separation Science (2015), 38(2), 205-210, database is CAplus and MEDLINE.

The C9-position of quinine was modified by meta- or para-substituted benzo-18-crown-6, and immobilized on 3-mercaptopropyl-modified silica gel through the radical thiol-ene addition reaction. These two chiral stationary phases were evaluated by chiral acids, amino acids, and chiral primary amines. The crown ether moiety on the quinine anion exchanger provided a ligand-exchange site for primary amino groups, which played an important role in the retention and enantioselectivity for chiral compounds containing primary amine groups. These two stationary phases showed good selectivity for some amino acids. The complex interaction between crown ether and protonated primary amino group was studied by the addition of inorganic salts such as LiCl, NH₄Cl, NaCl, and KCl to the mobile phase. The resolution results showed that the simultaneous interactions between two function moieties (quinine and crown ether) and amino acids were important for the chiral separation

Cheng, Ke’s team published research in Chinese Journal of Chemistry in 29 | CAS: 297752-25-1

Chinese Journal of 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 C20H21O4P, HPLC of Formula: 297752-25-1.

Cheng, Ke published the artcileChiral phosphoric acid catalyzed enantioselective allylation of aldehydes with allyltrichlorosilane, HPLC of Formula: 297752-25-1, the publication is Chinese Journal of Chemistry (2011), 29(8), 1669-1671, database is CAplus.

Easily accessible chiral phosphoric acid 1b has been applied as efficient organocatalyst for the asym. allylation of aldehydes with allyltrichlorosilane. In the presence of 20 mol% of 1b, the allylation of a broad range of aldehydes proceeded smoothly to give the corresponding homoallylic alc. with up to 87% ee and 97% yield.

Hrdina, Radim’s team published research in Organometallics in 32 | CAS: 297752-25-1

Organometallics 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 C20H21O4P, Formula: C20H21O4P.

Hrdina, Radim published the artcileSynthesis, Structural Analysis, and Catalytic Properties of Tetrakis(binaphthyl or octahydrobinaphthyl phosphate) Dirhodium(II,II) Complexes, Formula: C20H21O4P, the publication is Organometallics (2013), 32(2), 473-479, database is CAplus.

The x-ray structural analyses of homoleptic Rh(II) complexes made of enantiopure (R)-1,1′-binaphthyl and (R)-(5,5′,6,6′,7,7′,8,8′-octahydro)binaphthyl phosphate ligands are for the 1st time presented. The possibility to introduce halogen atoms at the 3,3′-positions is also reported. The isolated dirhodium complexes were further tested as catalysts (1 mol %) in enantioselective cyclopropanations and Si-H insertion reactions, affording chiral cyclopropanes and silanes in good yield but moderate enantioselectivity (ee maximum 63%).

Furuno, Hiroshi’s team published research in Tetrahedron in 59 | CAS: 297752-25-1

Tetrahedron 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 C20H21O4P, HPLC of Formula: 297752-25-1.

Furuno, Hiroshi published the artcileChiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels-Alder reactions, HPLC of Formula: 297752-25-1, the publication is Tetrahedron (2003), 59(52), 10509-10523, database is CAplus.

Various trivalent rare earth chiral phosphate complexes [ML₃] (L = I or II, R = H, 2,6-xylyl; M = Sc, La, Ce, Nd, Gd, Ho, Y) were prepared and evaluated as a Lewis acid catalyst for the asym. hetero-Diels-Alder reaction of aldehydes with the Danishefsky’s diene. Some of them effectively promoted the reaction at room temperature in the presence or absence of achiral additives under homogeneous conditions to afford the corresponding cycloadducts with high ee’s (up to 99% ee). During these reactions, remarkably high asym. amplifications (pos. nonlinear effects) were observed as the first example in the metal ion-chiral ligand 1:3 catalytic system. A scandium catalyst bearing the H₈-BNP ligand, [ScL₃] (L = II), could be recovered after the reaction and successfully reused for the next round of reactions. In addition, the hetero-Diels-Alder reaction of α-keto esters was effectively catalyzed by [YL₃] (L = I, R = H) without any additives thus producing the asym. quaternary carbon in excellent enantioselectivities (up to >99% ee).

He, Shanshan’s team published research in Chirality in 30 | CAS: 297752-25-1

Chirality 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 C20H21O4P, SDS of cas: 297752-25-1.

He, Shanshan published the artcileNovel chiral ionic liquids stationary phases for the enantiomer separation of chiral acid by high-performance liquid chromatography, SDS of cas: 297752-25-1, the publication is Chirality (2018), 30(5), 670-679, database is CAplus and MEDLINE.

Novel chiral ionic liquid stationary phases based on chiral imidazolium were prepared The ionic liquid chiral selector was synthesized by ring opening of cyclohexene oxide with imidazole or 5,6-dimethylbenzimidazole, and then chem. modified by different substitute groups. Chiral stationary phases were prepared by bonding to the surface of silica sphere through thioene “click” reaction. Their enantioselective separations of chiral acids were evaluated by high-performance liquid chromatog. The retention of acid sample was related to the counterion concentration and showed a typical ion exchange process. The chiral separation abilities of chiral stationary phases were greatly influenced by the substituent group on the chiral selector as well as the mobile phase, which indicated that, besides ion exchange, other interactions such as steric hindrance, π-π interaction, and hydrogen bonding are important for the enantioselectivity. In this report, the influence of bulk solvent components, the effects of varying concentration, and the type of the counterion as well as the proportion of acid and basic additives were investigated in detail.

Furuno, Hiroshi’s team published research in Tetrahedron Letters in 44 | CAS: 297752-25-1

Tetrahedron Letters 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 C20H21O4P, HPLC of Formula: 297752-25-1.

Furuno, Hiroshi published the artcileHighly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction, HPLC of Formula: 297752-25-1, the publication is Tetrahedron Letters (2003), 44(32), 6129-6132, database is CAplus.

Three types of rare earth (RE) complexes [Re((R)-BNP)₃] of (R)-1,1′-binaphthyl-2,2′-diylphosphates ((R)-BNP, 1; (R)-6,6′-xylyl-BNP, 2; (R)-H₈-BNP, 3) were synthesized and used as chiral Lewis acid catalysts for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky’s diene under homogeneous conditions. The Y[(R)-H₈-BNP]₃ (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP]₃ (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature The successful recycling uses of the scandium catalyst (3-Sc) are also described.