Khan, Hasan A.’s team published research in Chemical Science in 2011 | CAS: 256390-47-3

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Related Products of 256390-47-3 These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

Related Products of 256390-47-3On March 31, 2011, Khan, Hasan A.; Kou, Kevin G. M.; Dong, Vy M. published an article in Chemical Science. The article was 《Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of benzoxazecinones》. The article mentions the following:

A method for a nitrogen-directed ketone hydroacylation is reported to furnish eight-membered nitrogen-containing lactone (benzoxazecinone) derivatives in high yield and high enantiomeric excess. In a model study, a comparison was made between nitrogen, oxygen and sulfur directing groups and it was found that nitrogen promoted faster hydroacylation. By this catalytic transformation the synthesis of the target compounds (i.e., nitrogen heterocyclic compounds, benzoxazepinone derivatives and benzoxazecinone derivatives) was achieved and it was discovered that, moreover, an amine-directing group completely suppressed a competitive decarbonylation reaction. The experimental part of the paper was very detailed, including the reaction process of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Related Products of 256390-47-3)

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Related Products of 256390-47-3 These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Jiang, Yang-Jie’s team published research in Organic Letters in 2017 | CAS: 256390-47-3

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. SDS of cas: 256390-47-3 These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

SDS of cas: 256390-47-3On November 3, 2017 ,《Palladium-Catalyzed Asymmetric Allylic Alkylation of Alkyl-Substituted Allyl Reagents with Acyclic Amides》 appeared in Organic Letters. The author of the article were Jiang, Yang-Jie; Zhang, Gao-Peng; Huang, Jian-Qiang; Chen, Di; Ding, Chang-Hua; Hou, Xue-Long. The article conveys some information:

A wide range of alkyl-substituted allyl reagents, as well as nonstabilized carbon nucleophiles, was successfully used for the first time in the palladium-catalyzed asym. allylic alkylation reaction, affording the corresponding allylic alkylated products in high yields with high enantioselectivities. The usefulness of the protocol has been demonstrated by the enantioselective synthesis of an important chiral building block and enantiomer of Dubiusamine A. The experimental part of the paper was very detailed, including the reaction process of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3SDS of cas: 256390-47-3)

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. SDS of cas: 256390-47-3 These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Quintard, Adrien’s team published research in Organic Letters in 2019 | CAS: 210169-54-3

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Category: chiral-phosphine-ligands

In 2019,Organic Letters included an article by Quintard, Adrien; Rodriguez, Jean. Category: chiral-phosphine-ligands. The article was titled 《Enantioselective Ir-Catalyzed Bidirectional Reductive Coupling》. The information in the text is summarized as follows:

In the presence of a chiral iridium complex, com. available 3-chloro-2-chloromethyl-1-propene (1) was selectively activated for various reductive couplings. Depending on the reaction conditions it allows a selective mono- or bidirectional condensation with one or two external aldehydes with excellent enantiocontrol (>90% ee). This approach occurring simply under mild conditions and avoiding premetalated reagents constructs rapidly chiral homoallylic alcs., key precursors of important mol. fragments such as furans, pyrans, ketodiols, or 1,3,5-polyols. The results came from multiple reactions, including the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Category: chiral-phosphine-ligands)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Wang, Gang’s team published research in Nature Communications in 2019 | CAS: 210169-54-3

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Computed Properties of C38H28O4P2

The author of 《Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives》 were Wang, Gang; Xin, Xiaodong; Wang, Zehua; Lu, Gang; Ma, Yudao; Liu, Lei. And the article was published in Nature Communications in 2019. Computed Properties of C38H28O4P2 The author mentioned the following in the article:

A formal catalytic enantioselective cross-dehydrogenative coupling of saturated ethers with diverse carboxylic acid derivatives involving an initial oxidative acetal formation, followed by nickel(II)-catalyzed asym. alkylation. The one-pot, general and modular method exhibited wide compatibility of a broad range of saturated ethers not only including prevalent THF and tetrahydropyran but also including medium- and large-sized cyclic moieties and acyclic ones with excellent enantioselectivity and functional group tolerance. The application in the rapid preparation of biol. active mols. that are difficult to access with existing methods was also demonstrated. In addition to this study using (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, there are many other studies that have used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Computed Properties of C38H28O4P2) was used in this study.

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Computed Properties of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Wang, Cong-Shuai’s team published research in Organic Letters in 2021 | CAS: 210169-54-3

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Wang, Cong-Shuai; Wei, Liang; Fu, Cong; Wang, Xin-Heng; Wang, Chun-Jiang published their research in Organic Letters in 2021. The article was titled 《Asymmetric Synthesis of Axially Chiral Naphthyl-C3-indoles via a Palladium-Catalyzed Cacchi Reaction》.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article contains the following contents:

Atropoisomeric biaryl motifs are widely found in natural products and bioactive compounds as well as chiral catalysts and ligands. Various efficient approaches have been disclosed for the construction of chiral six-six biaryl skeletons. In contrast, the enantioselective synthesis of axially chiral arylindoles through the strategy of de novo construction, other than the asym. functionalization of indoles, remain a challenging task. Herein authors report an efficient Pd(0)/(S)-Segphos-catalyzed atroposelective Cacchi reaction of 2-alkynylanilines with sterically congested naphthyl halides, which afforded an array of naphthyl-C3-indoles in high yields with good to excellent atroposelectivities. The addition of water and the modulation of the manipulation procedure by premixing the palladium complex and the naphthyl halide were the keys to success. The conformational stability of the obtained axially chiral naphthyl-C3-indole containing a synthetically more-valuable free NH moiety is revealed through kinetic experiments The experimental process involved the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Huang, Yu-Hao’s team published research in Angewandte Chemie, International Edition in 2022-01-03 | 139139-93-8

Angewandte Chemie, International Edition published new progress about Crystal structure. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Product Details of C44H40P2.

Huang, Yu-Hao; Wu, Yichen; Zhu, Zile; Zheng, Sujuan; Ye, Zihang; Peng, Qian; Wang, Peng published the artcile< Enantioselective Synthesis of Silicon-Stereogenic Monohydrosilanes by Rhodium-Catalyzed Intramolecular Hydrosilylation>, Product Details of C44H40P2, the main research area is enantioselective regioselective preparation stereogenic cyclic monohydrosilane oxasilacycle; rhodium catalyzed intramol hydrosilylation; mol structure calculation cyclic monohydrosilane oxasilacycle; asymmetric synthesis; dihydrosilanes; hydrosilylation; monohydrosilane; rhodium.

Enantiopure monohydrosilanes are versatile chiral reagents for alc. resolution and mechanistic investigation. Herein, authors have demonstrated the asym. synthesis of monohydrosilanes via an intramol. hydrosilylation strategy. This protocol is suitable for the synthesis of five- and six-membered cyclic monohydrosilanes, including a class of chiral oxasilacycles, with excellent diastereo-, regio-, and enantioselectivities. Notably, the catalyst loading could be reduced to 0.1 mol % which makes this one of the most efficient methods to access chiral monohydrosilanes. Mechanistic studies and DFT calculations indicate this Rh-catalyzed intramol. asym. hydrosilylation reaction might proceed via a Chalk-Harrod mechanism, and the enantio-determining step was predicted to be oxidative addition of Si-H bond.

Angewandte Chemie, International Edition published new progress about Crystal structure. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Product Details of C44H40P2.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Hayashi, Tamio’s team published research in Angewandte Chemie, International Edition in 2004-11-19 | 139139-93-8

Angewandte Chemie, International Edition published new progress about Addition reaction catalysts, stereoselective. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Name: (S)-(-)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Hayashi, Tamio; Kawai, Masahiro; Tokunaga, Norihito published the artcile< Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines>, Name: (S)-(-)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is arylsulfonyl arylimine aryltitanium asym addition rhodium; arylamine arylsulfonyl stereoselective preparation desulfonylation; amine diarylmethyl stereoselective preparation.

Rhodium/chiral phosphine-catalyzed asym. addition of aryltitanium triisopropoxides to N-arylidene sulfonamides (Ar1CH=NSO2Ar2) yielded diarylmethyl arylsulfonamides, e.g., I, enantioselectively. A rational tuning of the arene sulfonamide moiety (by introducing iso-Pr groups onto the Ph ring) brought about high enantioselectivity in the reaction. Desulfonylation of the diarylmethyl arylsulfonamides yielded chiral diarylmethyl amines, e.g., II.

Angewandte Chemie, International Edition published new progress about Addition reaction catalysts, stereoselective. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Name: (S)-(-)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Tindall, Daniel J’s team published research in Angewandte Chemie, International Edition in 2021-01-11 | 139139-86-9

Angewandte Chemie, International Edition published new progress about Alditols Role: SPN (Synthetic Preparation), PREP (Preparation). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Synthetic Route of 139139-86-9.

Tindall, Daniel J.; Mader, Steffen; Kindler, Alois; Rominger, Frank; Hashmi, A. Stephen K.; Schaub, Thomas published the artcile< Selective and Scalable Synthesis of Sugar Alcohols by Homogeneous Asymmetric Hydrogenation of Unprotected Ketoses>, Synthetic Route of 139139-86-9, the main research area is stereoselective hydrogenation catalyst catalysis alditol monosaccharide ketose; asymmetric catalysis; hydrogenation; industrial chemistry; ruthenium; sugar alcohol.

Sugar alcs. are of great importance for the food industry and are promising building blocks for bio-based polymers. Industrially, they are produced by heterogeneous hydrogenation of sugars with H2, usually with none to low stereoselectivities. Now, we present a homogeneous system based on com. available components, which not only increases the overall yield, but also allows a wide range of unprotected ketoses to be diastereoselectively hydrogenated. Furthermore, the system is reliable on a multi-gram scale allowing sugar alcs. to be isolated in large quantities at high atom economy.

Angewandte Chemie, International Edition published new progress about Alditols Role: SPN (Synthetic Preparation), PREP (Preparation). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Synthetic Route of 139139-86-9.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Trost, Barry M’s team published research in Journal of the American Chemical Society in 2010-11-10 | 152140-65-3

Journal of the American Chemical Society published new progress about Aryl aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Safety of N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide].

Trost, Barry M.; Czabaniuk, Lara C. published the artcile< Palladium-Catalyzed Asymmetric Benzylation of 3-Aryl Oxindoles>, Safety of N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is aryloxindole enantioselective preparation; aralkyl carbonate aryloxindole asym benzylation palladium catalyst.

Palladium-catalyzed asym. benzylic alkylation with 3-aryl oxindoles as prochiral nucleophiles is reported. Proceeding analogously to asym. allylic alkylation, asym. benzylation occurs in high yield and enantioselectivity for a variety of unprotected 3-aryl oxindoles and benzylic Me carbonates using chiral bisphosphine ligands. This methodol. represents a novel asym. carbon-carbon bond formation between a benzyl group and a prochiral nucleophile to generate a quaternary center, e.g., I.

Journal of the American Chemical Society published new progress about Aryl aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Safety of N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide].

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Lavernhe, Remi’s team published research in Advanced Synthesis & Catalysis in 2020 | 152140-65-3

Advanced Synthesis & Catalysis published new progress about Allylic alkylation catalysts, stereoselective (decarboxylative). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, SDS of cas: 152140-65-3.

Lavernhe, Remi; Alexy, Eric J.; Zhang, Haiming; Stoltz, Brian M. published the artcile< Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates>, SDS of cas: 152140-65-3, the main research area is benzoin preparation enantioselective; allyl enol carbonate preparation decarboxylative allylic alkylation palladium catalyst; allylic alkylation; asymmetric catalysis; benzoin; palladium catalysis.

The enantioselective palladium-catalyzed decarboxylative allylic alkylation of fully substituted α-hydroxy acyclic enol carbonates (Z)-RC(OCO2allyl)=C(OMOM)R (R = C6H5, 2-naphthyl, 2H-1,3-benzodioxol-5-yl, etc.) providing tetrasubstituted benzoin derivatives (S)-RC(O)C(OMOM)(CH2CH=CH2)R is reported. Investigation into the transformation revealed that preparation of the starting material as a single enolate isomer is crucial for optimal enantioselectivity. The obtained alkylation products contain multiple reactive sites that can be utilized toward the synthesis of stereochem. rich derivatives

Advanced Synthesis & Catalysis published new progress about Allylic alkylation catalysts, stereoselective (decarboxylative). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, SDS of cas: 152140-65-3.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate