Tag: 300-400

Asymmetric iridium-catalyzed hydrogenation of 2-methylindole using phosphite ligands was written by Lyubimov, Sergey E.;Ozolin, Dmitry V.;Davankov, Vadim A.. And the article was included in Tetrahedron Letters in 2014.Synthetic Route of C24H22NO2P This article mentions the following:

The iridium-catalyzed asym. hydrogenation of 2-methylindole using monodentate phosphites and amidophosphites as ligands was examined The use of iodine as the additive resulted in increased enantioselectivity and conversion in the iridium-catalyzed hydrogenation of 2-methylindole. Full conversion and up to 80% ee were obtained with a catalyst based on a phosphite ligand. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Synthetic Route of C24H22NO2P).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) 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. Synthetic Route of C24H22NO2P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

PipPhos and MorfPhos: Privileged Monodentate Phosphoramidite Ligands for Rhodium-Catalyzed Asymmetric Hydrogenation was written by Bernsmann, Heiko;van den Berg, Michel;Hoen, Rob;Minnaard, Adriaan J.;Mehler, Gerlinde;Reetz, Manfred T.;de Vries, Johannes G.;Feringa, Ben L.. And the article was included in Journal of Organic Chemistry in 2005.Formula: C24H22NO2P This article mentions the following:

Chiral nonracemic monodentate phosphoramidites having binaphthalene and octahydrobinaphthalene backbones were prepared and showed excellent enantioselectivity in rhodium-catalyzed asym. hydrogenation of dehydroamino acids, itaconic acid and enamides. Reaction of (S)-1,1′-binaphthalene-2,2′-diol, (S)-C₂₀H₁₂(OH)₂ and (S)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthalene-2,2′-diol, (S)-C₂₀H₂₀(OH)₂ with PCl₃ and HNR₂ afforded a library of 20 monodentate phosphoramidite ligands (S)-C₂₀H₁₂O₂PNR₂ and (S)-C₂₀H₂₀O₂PNR₂ (1a–13a and 1b–11b, resp., R = Me, Et, n-Pr or R₂ = pyrrolidino, piperidino, hexahydro-1H-azepin-1-yl, morpholino, thiomorpholino, 4-phenyl-piperazin-1-yl, 1-indolinyl, 1,2,3,4-tetrahydro-2-isoquinolinyl, 2-alkoxycarbonyl-1-pyrrolidino). Asym. hydrogenation of Me 2-acetamidoacrylate, Me 2-acetamidocinnamate, di-Me itaconate and a number of N-acetyl enamines catalyzed by composition of [(cod)₂Rh]BF₄ and the phosphoramidites proceeds with high conversion and ee; specifically two ligands, PipPhos and MorfPhos [(S)-C₂₀H₁₂O₂PNR₂ R₂ = piperidino and morpholino, resp.] afford excellent and in several cases unprecedented enantioselectivities. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Formula: C24H22NO2P).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) 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.Formula: C24H22NO2P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rhodium-catalyzed enantioselective 1,4-additions of arylboronic acids to substituted enones was written by Mediavilla Urbaneja, Laura;Krause, Norbert. And the article was included in Tetrahedron: Asymmetry in 2006.Formula: C24H22NO2P This article mentions the following:

The rhodium-catalyzed enantioselective 1,4-addition of (aryl)boronic acids to bifunctional Michael acceptors in the presence of phosphoramidite ligands occurs regioselectively at the endocyclic carbon-carbon double bond and in up to 95% ee. The presence of KOH is required to increase the reactivity so that less boronic acid and lower reaction temperatures can be used. The corresponding addition to a chiral enone (i.e., 6-methyl-2-cyclohexen-1-one) takes place with epimerization of the product to the thermodynamically more stable trans-isomer, which was obtained with up to 98% ee. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Formula: C24H22NO2P).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Formula: C24H22NO2P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Catalytic asymmetric de novo construction of dihydroquinazolinone scaffolds via enantioselective decarboxylative [4+2] cycloadditions was written by Lu, Yi-Nan;Lan, Jin-Ping;Mao, Yu-Jia;Wang, Ye-Xin;Mei, Guang-Jian;Shi, Feng. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine This article mentions the following:

The first de novo construction of enantioenriched dihydroquinazolinones via an intermol. strategy was established. This approach also represented the first catalytic asym. [4+2] cycloaddition of vinyl benzoxazinanones with sulfonyl isocyanates, which afforded chiral dihydroquinazolinones in high yields and excellent enantioselectivities (up to 98% yield, 99 : 1 er). This reaction not only confronts the great challenge in de novo construction of enantioenriched dihydroquinazolinone skeletons, but also advances the chem. of decarboxylative cycloadditions involving vinyl benzoxazinanones. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

First rhodium/phosphoramidite complex-catalyzed enantioselective isomerization of allylic alcohols into aldehydes was written by Boeda, Fabien;Mosset, Paul;Crevisy, Christophe. And the article was included in Tetrahedron Letters in 2006.Electric Literature of C24H22NO2P This article mentions the following:

Primary allylic alcs. are converted into chiral aldehydes in the presence of a catalytic amount (7 mol %) of a monodentate phosphoramidite rhodium catalyst. The aldehydes are isolated in high yields (84-89%) and moderate to good ee’s (38-70%). A preliminary mechanistic study showed that the reaction proceeds through a 1,3-H migration pathway. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Electric Literature of C24H22NO2P).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Electric Literature of C24H22NO2P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Synthesis of chiral phosphorus reagents and their catalytic activity in asymmetric borane reduction of N-phenylimine of acetophenone was written by Li, Kangying;Zhou, Zhenghong;Zhao, Guofeng;Tang, Chuchi. And the article was included in Heteroatom Chemistry in 2003.Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine This article mentions the following:

Eleven chiral trivalent or quadrivalent phosphorus reagents were synthesized starting from L-proline, D-camphor, (+)- or (-)-1,1′-binaphthalene-2,2′-diol, (-)-α-phenylethylamine, etc. and their application as catalysts in asym. borane reduction of PhMeC:NPh was investigated. PhMeCHNHPh was obtained in good yield with low to moderate enantioselectivity. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

High Efficiency and Enantioselectivity in the Rh-Catalyzed Conjugate Addition of Arylboronic Acids Using Monodentate Phosphoramidites was written by Boiteau, Jean-Guy;Minnaard, Adriaan J.;Feringa, Ben L.. And the article was included in Journal of Organic Chemistry in 2003.Related Products of 252288-04-3 This article mentions the following:

A very fast reaction rates and high enantioselectivities were reached in the rhodium-catalyzed arylboronic acid addition to cyclic enones using a monodentate phosphoramidite ligand. Monodentate N,N-R₂-phosphoramidous esters of (S)-1,1′-binaphthyl-2,2′-diol and (S)-octahydro-1,1′-binaphthyl-2,2′-diol (L1-L4) were prepared by reaction of corresponding diol with PCl₃ followed by amination with NHR₂ (R = Me, Et). Asym. conjugate addition of arylboronic acids ArB(OH)₂ (Ar = Ph, 2-FC₆H₄, 3-MeOC₆H₄, 3-MeC₆H₄ 4-MeC₆H₄) to 2-cyclohexenone, 2-cyclopentanone, 2-cycloheptenone and 5,6-dihydro-2-pyranone in the presence of Rh(acac)(C₂H₄)₂/L4 (mol. ratio 1:2.5) gave corresponding 3-arylcycloalkanones and 4-phenyltetrahydro-2-pyranone with ee values > 96% (L4 = (S)-octahydro-1,1′-binaphthyl-2,2′-diyl N,N-diethylphosphoramidite). Temperature-dependent studies show that monodentate phosphoramidites form stable complexes with metals and can induce high enantioselectivities even at elevated temperatures in polar solvents. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Related Products of 252288-04-3).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) 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. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Related Products of 252288-04-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric hydrosilylation of cyclohexa-1,3-diene with trichlorosilane by palladium catalysts coordinated with chiral phosphoramidite ligands was written by Park, Hoon Seo;Han, Jin Wook;Shintani, Ryo;Hayashi, Tamio. And the article was included in Tetrahedron: Asymmetry in 2013.Formula: C24H22NO2P This article mentions the following:

Chiral phosphoramidite ligands prepared from (S)-binaphthol and secondary amines were examined for the palladium-catalyzed asym. hydrosilylation of cyclohexa-1,3-diene with trichlorosilane. With a sterically demanding phosphoramidite bearing bis(diphenylmethyl)amine, the high enantiomeric excess of 87% was achieved, which is the highest enantioselectivity in the hydrosilylation of cyclohexadiene reported to date. The catalytic activity in the present hydrosilylation was high with all of the ligands employed, while the enantioselectivities varied dramatically depending on the dialkylamine moiety of the phosphoramidite ligand. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Formula: C24H22NO2P).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Formula: C24H22NO2P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric hydrogenation of diethyl 1-phenylvinylphosphonate by metal complexes in CH₂Cl₂ and in supercritical carbon dioxide using phosphite-type ligands was written by Ozolin, D. V.;Lyubimov, S. E.;Davankov, V. A.. And the article was included in Russian Chemical Bulletin in 2014.Application In Synthesis of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine This article mentions the following:

Asym. hydrogenation of di-Et 1-phenylvinylphosphonate was carried out for the first time in dichloromethane and supercritical carbon dioxide in the presence of phosphite and amidophosphite ligands. The catalysts based on [Ir(COD)₂]BARF (COD is 1,5-cyclooctadiene, BARF is tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anion), provide higher enantioselectivity than [Ir(COD)Cl]₂ and [Rh(COD)₂]BF₄. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Application In Synthesis of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine).

(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Application In Synthesis of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis