Month: February 2023

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

Asymmetric Synthesis of C₂-Symmetric Axially Chiral Biaryls through Rhodium-Catalyzed and Alkyne-Controlled Diastereoselective Double [2+2+2]Cycloaddition was written by Mori, Ayaka;Araki, Tatsuya;Miyauchi, Yuta;Noguchi, Keiichi;Tanaka, Ken. And the article was included in European Journal of Organic Chemistry in 2013.Computed Properties of C29H30P2 This article mentions the following:

The asym. synthesis of C₂-sym. axially chiral biaryls was achieved by the cationic rhodium(I)/1,3-bis(diphenylphosphino)propane (dppp) complex catalyzed diastereoselective double [2+2+2]cycloaddition of (R)-3-butyn-2-ol-derived tetraynes with functionalized monoynes. Interestingly, the use of propiolate derivatives afforded biaryls possessing large dihedral angles, and in contrast, the use of propargyl alc. afforded biaryls possessing small dihedral angles. The title compounds thus formed included an isobenzofuran dimer (I) and related substances. Under optimized reaction conditions, the synthesis of the target compounds was achieved using bis(norbornadiene)rhodium(I) tetrafluoroborate and 1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine] as catalyst combination. The synthesis of the target compounds was achieved by a reaction of chiral 1,6-bis(2-butyn-1-yloxy)-2,4-hexadiyne, 1,6-bis(2-propyn-1-yloxy)-2,4-hexadiyne, 1,1′-[(2,4-hexadiyne-1,6-diyl)bis(oxy-1-propyne-3,1-diyl)]bis[benzene] with alkyne derivatives In the experiment, the researchers used many compounds, for example, (2S,4S)-Pentane-2,4-diylbis(diphenylphosphine) (cas: 77876-39-2Computed Properties of C29H30P2).

(2S,4S)-Pentane-2,4-diylbis(diphenylphosphine) (cas: 77876-39-2) 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. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Computed Properties of C29H30P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic 5,10-Dihydrophenazasilines via Enantioselective 1,5-Palladium Migration was written by Sato, Yosuke;Takagi, Chihiro;Shintani, Ryo;Nozaki, Kyoko. And the article was included in Angewandte Chemie, International Edition in 2017.Synthetic Route of C42H56FeO2P2 This article mentions the following:

A palladium-catalyzed asym. synthesis of silicon-stereogenic 5,10-dihydrophenazasilines was developed that proceeds via an unprecedented enantioselective 1,5-palladium migration. High enantioselectivity was achieved by employing 4,4′-bis(trimethylsilyl) (R)-Binap as the chiral ligand, and a series of mechanistic investigations were carried out to probe the catalytic cycle of this process. In the experiment, the researchers used many compounds, for example, (1R)-1-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene (cas: 360048-63-1Synthetic Route of C42H56FeO2P2).

(1R)-1-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene (cas: 360048-63-1) 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. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Synthetic Route of C42H56FeO2P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Efficient P,N,N-type ligands for Ru(II)-catalyzed asymmetric cyclopropanations was written by Dai, Huicong;Hu, Xiangping;Chen, Huilin;Bai, Changmin;Zheng, Zhuo. And the article was included in Journal of Molecular Catalysis A: Chemical in 2004.Formula: C26H28FeNP This article mentions the following:

Novel chiral P,N,N-type ligands I (R = Me, R¹ = H, Me; R = Et, Ph, R¹ = H) derived from (R)-(S)-PPFNH₂-R and 2-pyridinecarboxaldehydes were employed in Ru(II)-catalyzed asym. cyclopropanation of styrene with Et diazoacetate. Up to 99% yield with 95% e.e. for cis-isomer and 90% e.e. for trans-isomer was obtained on Ru(II)/I (R = Me, R¹ = H). In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2Formula: C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) 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.Formula: C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Dynamic kinetic asymmetric allylation of hydrazines and hydroxylamines was written by Mangion, Ian;Strotman, Neil;Drahl, Michael;Imbriglio, Jason;Guidry, Erin. And the article was included in Organic Letters in 2009.SDS of cas: 174810-09-4 This article mentions the following:

Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asym. allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic and heterocyclic amines and was applied toward a five-step synthesis of (R)-piperazic acid. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4SDS of cas: 174810-09-4).

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) 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. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.SDS of cas: 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

A general enantioselective route to the chamigrene natural product family was written by White, David E.;Stewart, Ian C.;Seashore-Ludlow, Brinton A.;Grubbs, Robert H.;Stoltz, Brian M.. And the article was included in Tetrahedron in 2010.Recommanded Product: (R)-2-(2-(Bis(4-(trifluoromethyl)phenyl)phosphino)-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole This article mentions the following:

Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds The generality of this strategy is demonstrated by the first total syntheses of elatol (I) and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and α-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. In the experiment, the researchers used many compounds, for example, (R)-2-(2-(Bis(4-(trifluoromethyl)phenyl)phosphino)-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole (cas: 1006708-91-3Recommanded Product: (R)-2-(2-(Bis(4-(trifluoromethyl)phenyl)phosphino)-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole).

(R)-2-(2-(Bis(4-(trifluoromethyl)phenyl)phosphino)-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole (cas: 1006708-91-3) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Recommanded Product: (R)-2-(2-(Bis(4-(trifluoromethyl)phenyl)phosphino)-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis