Month: December 2022

Asymmetric Friedel-crafts reaction of indole and cyclic enamine was written by Zhou, Jian-qing;Xu, Kai;Wang, Dan-jie;Cai, Zheng-yi;Gao, Jian-rong;Jia, Yi-xia. And the article was included in Zhejiang Huagong in 2013.Related Products of 1043567-32-3 This article mentions the following:

Friedel-Crafts alkylation reaction of 3-methylene-isoindol-1-one and indole catalyzed by chiral phosphoric acid was studied. With the optimization of catalyst, solvent and reaction temperature, the optimum catalyst was (S)-1-naphthyl replaced CPA-5 chiral phosphoric acid, optimum solvent was dichloromethane. The reaction could obtain 51% stereoselectivity under the room temperature Under these conditions, the substituent effect of indole was investigated, good reaction yield and 39%∼64% ee were obtained. 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: 1043567-32-3Related Products of 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. 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.Related Products of 1043567-32-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric Pauson-Khand reaction with chiral, electron-deficient mono- and bis-phosphine ligands was written by Konya, Denes;Robert, Frederic;Gimbert, Yves;Greene, Andrew E.. And the article was included in Tetrahedron Letters in 2004.HPLC of Formula: 252288-04-3 This article mentions the following:

The intermol. Pauson-Khand reaction between norbornene and dicobalt carbonyl complexes of phenylacetylene substituted with chiral phosphorus ligands has been investigated. I was obtained in high yield and good enantiomeric excess. 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. 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.HPLC of Formula: 252288-04-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Boryl-Dictated Site-Selective Intermolecular Allylic and Propargylic C-H Amination was written by Liu, Yuan;Chen, Zhi-Hao;Li, Yin;Qian, Jiasheng;Li, Qingjiang;Wang, Honggen. And the article was included in Journal of the American Chemical Society in 2022.SDS of cas: 252288-04-3 This article mentions the following:

For internal alkenes possessing two or more sets of electronically and sterically similar allylic protons, the site-selectivity for allylic C-H functionalization is fundamentally challenging. Previously, the neg. inductive effect from an electroneg. atom is effective for several inspiring regioselective C-H functionalization reactions. Yet, the use of an electropos. atom for a similar purpose remains to be developed. α-Aminoboronic acids and their derivatives found widespread applications. Their current syntheses rely heavily on functional group manipulations. Herein the authors report a boryl-directed intermol. C-H amination of allyl N-methyliminodiacetyl boronates (B(MIDA)s) and propargylic B(MIDA)s to give α-amino boronates with an exceptionally high level of site-selectivities (up to 300:1). A wide variety of highly functionalized secondary and tertiary α-amino boronates are formed in generally good to excellent yields, thanks to the mildness of the reaction conditions. The unsaturated double and triple bonds within the product leave room for further decorations. Mechanistic studies reveal that the key stabilization effect of the B(MIDA) moiety on its adjacent developing pos. charge is responsible for the high site-selectivity and that a closed transition state might be involved, as the reaction is fully stereoretentive. An activation effect of B(MIDA) is also found. 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: 252288-04-3SDS of cas: 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. SDS of cas: 252288-04-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Chiral Norbornadienes as Efficient Ligands for the Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Fumaric and Maleic Compounds was written by Shintani, Ryo;Ueyama, Kazuhito;Yamada, Ichiro;Hayashi, Tamio. And the article was included in Organic Letters in 2004.Recommanded Product: 252288-04-3 This article mentions the following:

A rhodium-catalyzed asym. 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions. In an example reaction, di-tert-Bu fumarate reacted with phenylboronic acid in the presence of (1R,4R)-2,5-di(2,4,6-trimethylphenylmethyl)bicyclo[2.2.1]hepta-2,5-diene giving (S)-di-tert-Bu phenylbutanedioate (90% yield, 90% ee). The structure of [RhCl(1)]₂ (1 = (1R,4R)-2,5-di(phenylmethyl)bicyclo[2.2.1]hepta-2,5-diene) was determined by x-ray crystallog. 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: 252288-04-3Recommanded Product: 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. 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. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Recommanded Product: 252288-04-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Diastereoselectively switchable enantioselective trapping of carbamate ammonium ylides with imines was written by Jiang, Jun;Xu, Hua-Dong;Xi, Jian-Bei;Ren, Bai-Yan;Lv, Feng-Ping;Guo, Xin;Jiang, Li-Qin;Zhang, Zhi-Yong;Hu, Wen-Hao. And the article was included in Journal of the American Chemical Society in 2011.Computed Properties of C48H29O4P This article mentions the following:

The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh₂(OAc)₄ and chiral Bronsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-α-substituted α,β-diamino acid derivatives e. g., I and II with a high level control of chemo-, diastereo-, and 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: 1043567-32-3Computed Properties 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. 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.Computed Properties of C48H29O4P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium-catalyzed asymmetric [3 + 3] cycloaddition of trimethylenemethane derivatives with nitrones was written by Shintani, Ryo;Park, Soyoung;Duan, Wei-Liang;Hayashi, Tamio. And the article was included in Angewandte Chemie, International Edition in 2007.Recommanded Product: (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine This article mentions the following:

Functionalized 1,2-oxazines can be obtained in high yield by a palladium-catalyzed asym. [3 + 3] cycloaddition of trimethylenemethane derivatives with nitrones. The use of a modified phosphoramidite ligand has led to the formation of these compounds with high stereoselectivity (see scheme, Cp = cyclopentadienyl). 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: 252288-04-3Recommanded Product: (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. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Recommanded Product: (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Catalytic asymmetric synthesis of N-substituted tetrahydroquinoxalines via regioselective Heyns rearrangement and stereoselective transfer hydrogenation in one pot was written by Huang, Jin;Li, Guang-xun;Yang, Gao-feng;Fu, Ding-qiang;Nie, Xiao-kang;Cui, Xin;Zhao, Jin-zhong;Tang, Zhuo. And the article was included in Chemical Science in 2021.HPLC of Formula: 1043567-32-3 This article mentions the following:

N-Substituted tetrahydroquinoxalines (37 examples) were step-economically obtained in good yield (<97%) and ee (<99%) with readily available substrates. The reaction proceeded through an interesting regioselective Heyns rearrangement/enantioselective transfer hydrogenation in one pot. The substrate scope and the reaction mechanism were systematically investigated. 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. 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.HPLC of Formula: 1043567-32-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

A Novel Method for Synthesizing N-Alkoxycarbonyl Aryl α-Imino Esters and Their Applications in Enantioselective Transformations was written by Qian, Yu;Jing, Changcheng;Zhai, Changwei;Hu, Wen-hao. And the article was included in Advanced Synthesis & Catalysis in 2012.Safety 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:

A new strategy for the synthesis of N-alkoxycarbonyl aryl α-imino esters in the presence of dirhodium tetraacetate [Rh₂(OAc)₄] is reported to produce the desired compounds in high yield (up to 96%) under mild reaction conditions. The application of the synthetic method is demonstrated in enantioselective reduction and Friedel-Crafts reaction of indoles to afford the corresponding chiral arylglycines and indole derivatives, resp., in high yield and excellent ee. 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: 1043567-32-3Safety 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. 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. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Safety 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

Enantioselective Synthesis of Tetrahydroindolizines via Ruthenium-Chiral Phosphoric Acid Sequential Catalysis was written by Zhou, Yong;Liu, Xiao-Wei;Gu, Qing;You, Shu-Li. And the article was included in Synlett in 2016.Computed Properties of C48H29O4P This article mentions the following:

A chiral phosphoric acid and a ruthenium complex were found to catalyze an olefin cross-metathesis-asym. intramol. Friedel-Crafts alkylation of N-tethered olefin pyrroles and conjugated enones to provide a variety of chiral tetrahydroindolizine derivatives in moderate to good yields and enantioselectivity (up to 93% ee). Under optimized conditions the synthesis of the target compounds was achieved using (11bS)-4-hydroxy-2,6-bis(9-phenanthrenyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin 4-oxide (i.e., chiral cyclic phosphate analog) and [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro[[5-[(dimethylamino)sulfonyl]-2-(1-methylethoxy-κO)phenyl]methylene-κC]ruthenium (i.e., Zhan-1B) as ligand and catalyst combination. The synthesis of the target compounds was achieved by a reaction of 1-(4-pentenyl)-2-phenyl-1H-pyrrole derivatives with 1-phenyl-2-propen-1-one derivatives, 3-Buten-2-one, (2E)-1-phenyl-2-buten-1-one. The tilte compounds thus formed included a chiral pyrrolo[1,2-d][1,4]oxazepine derivative and (indolizinyl)(aryl)ethanone derivatives 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: 1043567-32-3Computed Properties 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. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Computed Properties of C48H29O4P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Formal Asymmetric Organocatalytic [3+2] Cyclization between Enecarbamates and 3-Indolylmethanols: Rapid Access to 3-Aminocyclopenta[b]indoles was written by Lebee, Clement;Kataja, Antti O.;Blanchard, Florent;Masson, Geraldine. And the article was included in Chemistry – A European Journal in 2015.Category: chiral-phosphine-ligands This article mentions the following:

A highly enantio- and diastereoselective synthesis of 3-aminocyclopenta[b]indoles I [R¹ = Me, Et, CHMe₂, cyclopropyl, CH₂CHMe(CH₂)₂CH:CMe₂-(S), (CH₂)₃OSiPh₂CMe₃, R² = CH₂Ph, R³ = Ph, R⁴ = R⁵ = H; R¹ = Me, R² = CMe₃, R³ = Ph, R⁴ = R⁵ = H; R¹ = Me, R² = CH₂Ph, R³ = C₆H₄F-4, C₆H₄F-3, C₆H₄F-2, C₆H₄CF₃-4, C₆H₄OMe-3, 2-naphthyl, 2-thienyl, CHMe₂, Bu, R⁴ = R⁵ = H; R¹ = Me, R² = CH₂Ph, R³ = Ph, R⁴ = OMe-5, Br-5, Br-6, R⁵ = H; R¹ = Me, R² = R⁵ = CH₂Ph, R³ = Ph, R⁴ = H] has been developed through formal [3+2] cycloaddition reaction of enecarbamates, (E)-R¹CH:CHCO₂R², and 3-indolylmethanols, II. This transformation is catalyzed by a chiral phosphoric acid that achieves simultaneous activation of both partners of the cycloaddition Mechanistic data are also presented that suggest that the reaction occurs through a stepwise pathway. 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. 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.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis