Day: February 23, 2023

Synthesis of benzannulated spiroacetals using chiral gold-phosphine complexes and chiral anions was written by Quach, Rachelle;Furkert, Daniel P.;Brimble, Margaret A.. And the article was included in Tetrahedron Letters in 2013.Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) This article mentions the following:

The development of an asym. gold-catalyzed dihydroalkoxylation strategy for the synthesis of the 3’H-spiro[chroman-2,1′-isobenzofuran] spiroketal ring system I is described. Spiroacetal I was generated in up to 87:13 enantiomeric ratio using chiral gold-phosphine complexes and chiral silver phosphate Ag(S)-TRIP. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification was written by Zhao, Jianchao;Wu, Haixia;Wang, Dongqiang;Wu, Haibo;Cheng, Lingping;Jin, Yu;Ke, Yanxiong;Liang, Xinmiao. And the article was included in Journal of Separation Science in 2015.Related Products of 297752-25-1 This article mentions the following:

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. In the experiment, the researchers used many compounds, for example, (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 297752-25-1Related Products of 297752-25-1).

(R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 297752-25-1) belongs to chiral phosphine ligands. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Related Products of 297752-25-1

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Regio- and Stereoselective Synthesis of Key 1-Methyl Carbapenem Intermediates via Hydroformylation Using a Zwitterionic Rhodium Catalyst was written by Park, H. S.;Alberico, E.;Alper, H.. And the article was included in Journal of the American Chemical Society in 1999.Safety of (2S,4S)-Pentane-2,4-diylbis(diphenylphosphine) This article mentions the following:

The asym. hydroformylation of a 4-vinyl β-lactam catalyzed by a rhodium catalyst with a chiral phosphine ligand was investigated. The catalytic system consisting of a zwitterionic rhodium catalyst, (NBD)Rh⁺(C₆H₅B^–Ph₃), and (S,S)-2,4 bis(diphenylphosphino)pentane, (S,S)-BDPP, gave branched aldehydes in high regio- and stereoselectivity. The hydroformylated products are key intermediates in the synthesis of 1-methylcarbapenem antibiotics. Using (3S,4R)-3-[(R)-1-(tert-butyldimethyl-silyloxy)ethyl]-4-vinyl-2-azetidinone as the reactant afforded aldehydes in a 97:3 branched-to-linear ratio and 91:9 to β- to α-branched isomers. The regio (branched/linear)- and stereoselectivity (β/α) was >99:1 when (3S,4R)-1-N-BOC-3-[(R)-1-methoxyethyl]-4-vinyl-2-azetidinone was used as the substrate. In the experiment, the researchers used many compounds, for example, (2S,4S)-Pentane-2,4-diylbis(diphenylphosphine) (cas: 77876-39-2Safety of (2S,4S)-Pentane-2,4-diylbis(diphenylphosphine)).

(2S,4S)-Pentane-2,4-diylbis(diphenylphosphine) (cas: 77876-39-2) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Safety of (2S,4S)-Pentane-2,4-diylbis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium-catalyzed asymmetric carbamoyl-carbonylation of alkenes was written by Feng, Ziwen;Li, Qiuyu;Chen, Long;Yao, Hequan;Lin, Aijun. And the article was included in Science China: Chemistry in 2021.Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) This article mentions the following:

An unprecedented palladium-catalyzed asym. carbamoyl-carbonylation of tethered alkenes with CO and alcs. was developed. This reaction provided an efficient route to access oxindoles I [R¹ = Me, Ph, 2-thienyl, etc.; R² = Me, i-Pr, Bn; R³ = Me, Et, CH₂CH₂TMS, etc.] and γ-lactams bearing β-carbonyl substituted quaternary carbons II [Ar = Ph, 3-MeC₆H₄, 4-MeOC₆H₄, 4-CF₃C₆H₄, 3-ClC₆H₄, 4-ClC₆H₄] in good yields with excellent chemo-, regio- and enantioselectivity. Gram-scale synthetic capability and facile transformations of the products to chiral spirooxindole and other functional mols. further illustrated the practicability of this reaction. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Low-pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes was written by Movahhed, Sohajl;Westphal, Julia;Dindaroglu, Mehmet;Falk, Anna;Schmalz, Hans-Guenther. And the article was included in Chemistry – A European Journal in 2016.Formula: C24H20NO3P This article mentions the following:

An efficient and practical protocol for the enantioselective cobalt-catalyzed hydrovinylation of vinylarenes with ethylene at low (1.2 bar) pressure was developed. As precatalysts, stable [L₂CoCl₂] complexes were employed that were activated in situ with Et₂AlCl. A modular chiral TADDOL-derived phosphine-phosphite ligand was identified and that allowed the conversion of a broad spectrum of substrates including heterocyclic vinylarenes and vinylferrocene to smoothly afford the branched products with up to 99 % ee and virtually complete regioselectivity. Even polar functional groups such as OH, NH₂, CN, and CO₂R were tolerated. In the experiment, the researchers used many compounds, for example, (S)-4-(Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl)morpholine (cas: 185449-81-4Formula: C24H20NO3P).

(S)-4-(Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl)morpholine (cas: 185449-81-4) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Formula: C24H20NO3P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Enantioselective Synthesis of Planar-Chiral Carba-Paracyclophanes: Rhodium-Catalyzed [2+2+2] Cycloaddition of Cyclic Diynes with Terminal Monoynes was written by Araki, Tatsuya;Noguchi, Keiichi;Tanaka, Ken. And the article was included in Angewandte Chemie, International Edition in 2013.Related Products of 37002-48-5 This article mentions the following:

The high-yielding and highly enantioselective synthesis of carba[10]-[12]paracyclophanes I [X = (CH₂)_n; n = 7-9; R¹ = Ts, 2-O₂NC₆H₄SO₂; R² = MeO₂C, HOCH₂, n-Bu, MeCH(OH), etc.] has been achieved with up to 93% ee by the cationic rhodium(I)/(S,S)-bdpp-catalyzed [2 + 2 + 2] cycloaddition of cyclic diynes II and terminal alkynes R²CCH under high substrate concentrations [bdpp = 2,4-bis(diphenylphosphino)pentane]. In the experiment, the researchers used many compounds, for example, (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5Related Products of 37002-48-5).

(((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5) belongs to chiral phosphine ligands. Many phosphine-catalyzed reactions have been developed for the syntheses of various biologically important acyclic and cyclic molecules. Asymmetric variants of these reactions have evolved relatively slowly. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Related Products of 37002-48-5

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Access to trans-3,4-Dihydroxy-2-alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic N,O-Acetals as a Diversity-Generating Element was written by Kang, Soyeong;Kim, Dong-gil;Rhee, Young Ho. And the article was included in Chemistry – A European Journal in 2014.Quality Control of N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) This article mentions the following:

A highly efficient and stereoselective synthetic pathway towards trans-3,4-dihydroxy-2-alkylpyrrolidines and piperidines I (n = 1, 2; A = CO, C(C₂H₅)₂; R = CH₂COPh, CH₂CCH, CN, etc.) is described. The nature of the protecting groups on the hydroxyl moieties played a crucial role on the trans selectivity. By using this method, a concise total synthesis of (-)-2-epilentiginosine has been achieved. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Quality Control of N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)).

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Quality Control of N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric hydrogenation of quinolines activated by Bronsted acids was written by Wang, Duo-Sheng;Zhou, Yong-Gui. And the article was included in Tetrahedron Letters in 2010.Application In Synthesis of (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) This article mentions the following:

Enantioselective hydrogenation of quinolines and quinoxalines catalyzed by iridium/diphosphine complex with a catalytic amount of Bronsted acid as an activator was developed. In the presence of piperidine·trifluoromethanesulfonic acid as the activator, full conversions and up to 92% ee were obtained. In the experiment, the researchers used many compounds, for example, (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5Application In Synthesis of (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine)).

(((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Application In Synthesis of (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Nickel-Catalyzed Intramolecular Arylcyanation for the Synthesis of 3,3-Disubstituted Oxindoles was written by Yen, Andy;Lautens, Mark. And the article was included in Organic Letters in 2018.Recommanded Product: (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) This article mentions the following:

In the presence of NiCl₂(glyme), (S,S)-DIOP, and Zn, N-(bromophenyl)-N-methylacrylamides such as I underwent intramol. arylcyanation reactions with Zn(CN)₂ in MeCN to yield oxoindolylacetonitriles (3,3-disubstituted oxindoles) such as II in 30-86% yields. In the experiment, the researchers used many compounds, for example, (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5Recommanded Product: (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine)).

(((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Recommanded Product: (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Copper-Catalyzed Asymmetric Borylative Ring Opening of Diazabicycles was written by Lee, Hyesu;Han, Jung Tae;Yun, Jaesook. And the article was included in ACS Catalysis in 2016.HPLC of Formula: 174467-31-3 This article mentions the following:

Highly enantioselective, copper-catalyzed ring opening of bicyclic hydrazines using a diboron reagent was accomplished with (R,R)-taniaphos as a chiral ligand. Desymmetrization of various bicyclic hydrazines by boryl substitution afforded 3-Bpin-4-hydrazino-cyclopentene derivatives with enantioselectivity up to >99% under mild conditions. The resulting allylic boron products were utilized in further organic transformations. Kinetic resolution of a racemic bicyclic oxazine gave useful information about the relative rates of C-O and C-N bond cleavage. In the experiment, the researchers used many compounds, for example, (R,R)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-bis(diphenylphosphino)ferrocene (cas: 174467-31-3HPLC of Formula: 174467-31-3).

(R,R)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-bis(diphenylphosphino)ferrocene (cas: 174467-31-3) belongs to chiral phosphine ligands. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.HPLC of Formula: 174467-31-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis