Day: December 30, 2022

Tandem Ir-Catalyzed Allylic Substitution Reaction of Allyl Sulfinates and Isomerization was written by Xu, Qing-Long;Dai, Li-Xin;You, Shu-Li. And the article was included in Organic Letters in 2010.Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine This article mentions the following:

An efficient method for the synthesis of trisubstituted vinyl sulfones is reported. Using the [Ir(COD)Cl]₂/phosphoramidite ligand/DBU, trisubstituted vinyl sulfones could be synthesized from allyl sulfinates in high yields as exclusively E isomers. 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. 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.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

Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; ligand variation and non-linear effects was written by Arnold, Leggy A.;Imbos, Rosalinde;Mandoli, Alessandro;De Vries, Andre H. M.;Naasz, Robert;Feringa, Ben L.. And the article was included in Tetrahedron in 2000.COA of Formula: C24H22NO2P This article mentions the following:

A variety of new chiral phosphoramidites was synthesized and tested in the copper-catalyzed enantioselective conjugate addition of Et₂Zn to cyclohexenone and chalcone to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.’s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic and acyclic enones. 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: 252288-04-3COA of Formula: 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. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.COA of Formula: C24H22NO2P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric 1,4-addition of organoboron reagents to quinone monoketals catalyzed by a chiral diene/rhodium complex: a new synthetic route to enantioenriched 2-aryltetralones was written by Tokunaga, Norihito;Hayashi, Tamio. And the article was included in Advanced Synthesis & Catalysis in 2007.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:

A novel synthetic approach to 2-aryltetralones with high ee has been developed through asym. 1,4-addition of arylboronic acids to naphthoquinone monoketals catalyzed by a rhodium complex with the (R,R)-Ph-bod* ligand. The asym. addition proceeded in high yields with excellent 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: 252288-04-3Application 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. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.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

Asymmetric Friedel-Crafts reaction of 4,7-dihydroindoles with nitroolefins by chiral Bronsted acids under low catalyst loading was written by Sheng, Yi-Fei;Li, Gong-Qiang;Kang, Qiang;Zhang, An-Jiang;You, Shu-Li. And the article was included in Chemistry – A European Journal in 2009.Synthetic Route of C48H29O4P This article mentions the following:

By adding the substrate by a syringe pump, a highly efficient Friedel-Crafts reaction of 4,7-dihydroindoles with nitroolefins was realized with 0.5 mol% of a chiral phosphoric acid. The Friedel-Crafts alkylation, together with a subsequent oxidation of the product, led to 2-substituted indoles in excellent enantiomeric excesses, which can be easily transformed to enantio-enriched tetrahydro-γ-carbolines. In the experiment, the researchers used many compounds, for example, (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3Synthetic Route of C48H29O4P).

(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Synthetic Route of C48H29O4P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric counteranion-directed transition-metal catalysis: enantioselective epoxidation of alkenes with manganese(III) salen phosphate complexes was written by Liao, Saihu;List, Benjamin. And the article was included in Angewandte Chemie, International Edition in 2010.HPLC of Formula: 1043567-32-3 This article mentions the following:

Epoxides e. g. I, were prepared through enantioselective epoxidation of olefins catalyzed by Mn-salen complex and chiral phosphate counterion system, which represents another powerful application of the concept of asym. counteranion-directed catalysis. In the experiment, the researchers used many compounds, for example, (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3HPLC of Formula: 1043567-32-3).

(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.HPLC of Formula: 1043567-32-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Bronsted Acid-Promoted Friedel-Crafts Alkylation/Cyclization of (7-Hydroxynaphthalenyl)pyrrole or (2-Hydroxyphenyl)pyrroles with Isatins for the Construction of Pyrrolospirooxindole Derivatives was written by Gao, Zeng;Zhang, Jinlong;Yang, Huameng;Jiang, Gaoxi. And the article was included in Journal of Organic Chemistry in 2018.Application In Synthesis of (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide This article mentions the following:

An efficient trifluoroacetic acid-catalyzed cascade Friedel-Crafts alkylation/cyclization of 1-(7-hydroxynaphthalenyl)pyrrole or 1-(2-hydroxyphenyl)pyrroles with isatins has been developed, providing practical access to a variety of biol. important pyrrole-containing spirooxindoles. In the experiment, the researchers used many compounds, for example, (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3Application In Synthesis of (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide).

(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Application In Synthesis of (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Chiral phosphoric acid catalyzed asymmetric hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones was written by Zhou, Jian-Qing;Sheng, Wei-Jian;Jia, Jian-Hong;Ye, Qing;Gao, Jian-Rong;Jia, Yi-Xia. And the article was included in Tetrahedron Letters in 2013.Recommanded Product: 1043567-32-3 This article mentions the following:

The enantioselective hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones catalyzed by BINOL-derived chiral phosphoric acid with benzothiazoline as the hydride source is described. The corresponding cyclic diaryl methylamines, 3-arylisoindolin-1-ones, are obtained in good to excellent yields and ≤91% enantioselectivity. In the experiment, the researchers used many compounds, for example, (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3Recommanded Product: 1043567-32-3).

(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3) 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. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.Recommanded Product: 1043567-32-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rh(II)/Bronsted Acid Catalyzed General and Highly Diastereo- and Enantioselective Propargylation of in Situ Generated Oxonium Ylides and C-Alkynyl N-Boc N,O-Acetals: Synthesis of Polyfunctional Propargylamines was written by Meng, Xueling;Yang, Binmiao;Zhang, Linxing;Pan, Guangyao;Zhang, Xinhao;Shao, Zhihui. And the article was included in Organic Letters in 2019.Category: chiral-phosphine-ligands This article mentions the following:

The first metal/organo cooperatively catalyzed asym. reaction of C-alkynyl N-Boc-protected N,O-acetals with in situ generated oxonium ylides has been developed. This new type of propargylation allows for the efficient synthesis of structurally diverse unreported chiral propargylamines bearing oxa-quaternary stereocenters. The reaction features unprecedented substrate scope and high diastereo- and enantioselectivity. Theor. studies suggest a novel cooperative catalysis model and the unique transfer of R²OH. In the experiment, the researchers used many compounds, for example, (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3Category: chiral-phosphine-ligands).

(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide (cas: 1043567-32-3) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Highly Efficient Rhodium/Monodentate Phosphoramidite Catalyst and Its Application in the Enantioselective Hydrogenation of Enamides and α-Dehydroamino Acid Derivatives was written by Jia, Xian;Li, Xingshu;Xu, Lijin;Shi, Qian;Yao, Xinsheng;Chan, Albert S. C.. And the article was included in Journal of Organic Chemistry in 2003.HPLC of Formula: 252288-04-3 This article mentions the following:

An easily prepared and highly efficient monodentate phosphoramidite ligand (S)-2,2′-O,O-(1,1′-binaphthyl)-dioxo-N,N-diethylphospholidine, derived from BINOL, was examined in the hydrogenation of both enamides H₂C:CR¹NHCOMe (R¹ = Ph, 4-F₃CC₆H₄, 3-MeOC₆H₄, 1-naphthyl, etc.) and α-dehydroamino acid esters R²CH:C(NHR³)CO₂Me (R² = H, Ph, 4-FC₆H₄, 4-MeOC₆H₄, etc.; R³ = MeCO, PhCO). The catalyst provided remarkably high enantioselectivities (up to 99.6% ee for enamides and >99.9% ee for α-dehydroamino acid esters). 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: 252288-04-3HPLC of Formula: 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. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. HPLC of Formula: 252288-04-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes was written by Kurihara, Kazunori;Sugishita, Noriyuki;Oshita, Kengo;Piao, Dongguo;Yamamoto, Yasunori;Miyaura, Norio. And the article was included in Journal of Organometallic Chemistry in 2007.Safety of (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine This article mentions the following:

A chiral bidentate phosphoramidites I and their rhodium complexes were prepared by esterification of the corresponding linked BINOLs with phosphorous triamides; the complexes exhibit high activity and stereoselectivity in asym. conjugate addition of arylboronic acids to α,β-unsaturated ketones. Reaction of Shibasaki’s linked-(R)-BINOL, (R,R)-3,3”-oxybis(methylene)bis[1,1′-binaphthalene-2,2′-diol], with P(NR₂)₃ gave bis-phosphoramidites I (5a–c; R = Me, Et, ⁱPr); rhodium(I) complexes of 5a [(L)Rh(nbd)]BF₄ and [(L)RhCl] (7a, b) were prepared by complexation of [Rh(nbd)₂]BF₄ and [Rh(coe)Cl], resp. Phosphoramidites 5a–c were used as new ligands for rhodium(I)-catalyzed asym. 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds 2-Cyclohexenone, 2-cyclopentenone, 2-cycloheptenone, (E)-R¹CH:CHCOR² (R¹ = C₅H₁₁, ⁱPr, Ph; R² = Me, Ph, C₆H₁₁) undergo asym. 1,4-addition of ArB(OH)₂ (Ar = Ph, 3-MeOC₆H₄, 4-MeOC₆H₄, 3-ClC₆H₄, 3-FC₆H₄, 4-MeC₆H₄) catalyzed by Rh(I) complexes with ligands I, giving the corresponding 3-substituted ketones with high yields and enantioselectivities up to 99.6 ee. The effects of 5a and Feringa’s monodentate phosphoramidite, (S)-C₂₀H₁₂O₂PNR³R⁴ (4, C₂₀H₁₂ = 1,1′-binaphthalene-2,2′-diyl; R³ = R⁴ = Me, Et, PhCH₂, ⁱPr, R³-R⁴ = (CH₂)₅, CH₂CH₂NHCH₂CH₂; R³, R⁴: Me, Et; Me, Pr; Me, PhCH₂; Me, Ph; Me, ⁱPr; Me, 1-adamantyl; Me, ^tBu) on the yields and enantioselectivities evaluated. The reaction was significantly accelerated in the presence of a base such as KOH and Et₃N, allowing the reaction to be completed at ambient temperature The addition to cyclic enones such as 2-cyclopentenone, 2-cyclohexenone and 2-cycloheptenone at 50° in the presence of an [Rh(coe)₂Cl]₂–4 (R³, R⁴ = Et) resulted in enantioselectivities up to 98%, though it was less effective for acyclic enones (0-70% ee). On the other hand, the complex 7a completed the addition to cyclic enones within 2 h at room temperature in the presence of Et₃N with 86-99% yields and 96-99.8% ee. This catalyst was also effective for acyclic enones, resulting in 62-98% yields and 66-94% ee. The 1,4-additions of arylboronic acids to unsaturated lactones and acyclic esters with rhodium(I)-phosphoramidites complexes were also investigated. 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. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. 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