Tanaka, Rie’s team published research in Journal of the American Chemical Society in 2010-02-03 | 139139-86-9

Journal of the American Chemical Society published new progress about Alkynals Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Related Products of 139139-86-9.

Tanaka, Rie; Noguchi, Keiichi; Tanaka, Ken published the artcile< Rhodium-catalyzed asymmetric reductive cyclization of heteroatom-linked 5-alkynals with heteroatom-substituted acetaldehydes>, Related Products of 139139-86-9, the main research area is heteroatom alkynal acetaldehyde rhodium catalyst asym reductive cyclization.

We have established that a cationic rhodium(I)/H8-BINAP complex catalyzes the asym. reductive cyclization of heteroatom-linked 5-alkynals with heteroatom-substituted acetaldehydes in good yields with outstanding enantioselectivity.

Journal of the American Chemical Society published new progress about Alkynals Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Related Products 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

Suda, Takeshi’s team published research in Angewandte Chemie, International Edition in 2011 | 139139-86-9

Angewandte Chemie, International Edition published new progress about Alkadiynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Product Details of C44H40P2.

Suda, Takeshi; Noguchi, Keiichi; Tanaka, Ken published the artcile< Rhodium-Catalyzed Asymmetric Formal Olefination or Cycloaddition: 1,3-Dicarbonyl Compounds Reacting with 1,6-Diynes or 1,6-Enynes>, Product Details of C44H40P2, the main research area is dicarbonyl stereoselective olefination diyne enyne rhodium BINAP segphos catalyst.

The Rh(I)/(R)-H8-BINAP complex was used as the catalyst in the asym. intermol. olefination of enolizable 1,3-dicarbonyl compounds with 1,6-diynes by [2+2+2]cycloaddition followed by electrocyclic ring opening. The same reaction was also accomplished with 1,6-enynes by using Rh(I)/S-segphos as catalyst.

Angewandte Chemie, International Edition published new progress about Alkadiynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 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

Tanaka, Ken’s team published research in Angewandte Chemie, International Edition in 2009 | 139139-86-9

Angewandte Chemie, International Edition published new progress about Alkadiynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, COA of Formula: C44H40P2.

Tanaka, Ken; Fukawa, Naohiro; Suda, Takeshi; Noguchi, Keiichi published the artcile< One-Step Construction of Five Successive Rings by Rhodium-Catalyzed Intermolecular Double [2+2+2] Cycloaddition: Enantioenriched [9]Helicene-Like Molecules>, COA of Formula: C44H40P2, the main research area is tetrayne diyne intermol cycloaddition rhodium catalyst; helicene asym preparation crystal mol structure.

The synthesis of [9]helicene-like mols. by rhodium-catalyzed intermol. double [2+2+2] cycloadditions is presented. Crystal structure and photophys. data for the compounds are also determined

Angewandte Chemie, International Edition published new progress about Alkadiynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, COA of Formula: 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

Zhang, Xiaoyong’s team published research in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1994-08-21 | 139139-86-9

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Crystal structure. 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Safety of (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Zhang, Xiaoyong; Mashima, Kazushi; Koyano, Kinko; Sayo, Noboru; Kumobayashi, Hidenori; Akutagawa, Susumu; Takaya, Hidemasa published the artcile< Synthesis of partially hydrogenated 2,2'-bis(diphenylphosphenyl)-1,1'-binaphthyl (BINAP) ligands and their application to catalytic asymmetric hydrogenation>, Safety of (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is bisphosphine chiral partially hydrogenated synthesis ligand; ruthenium catalyst hydrogenation chiral phosphine ligand; asym hydrogenation ruthenium catalyst chiral phosphine; crystal structure chiral diphosphine ruthenium cation; mol structure chiral diphosphine ruthenium cation.

Three pairs of new axially dissym. bisphosphine ligands, (R)-(-)- and (S)-(+)-2,2′-bis(dicyclohexylphosphinyl)-1,1′-binaphthyl [ I, R = C6H11], (R)-(+)- and (S)-(-)-2,2′-bis(diphenylphosphinyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl [II, R = Ph], and (R)-(-)- and (S)-(+)-2,2′-bis(dicyclohexylphosphinyl)-5,5′,6,6,7,7′,8,8′-octahydro-1,1′-binaphthyl [II, R = C6H11], have been synthesized. The absolute configurations of the isomers I were determined by single-crystal x-ray diffraction of the linear 1:1 polymeric complex of (S)-(+)-2,2′-bis(dicyclohexylphosphinoyl)-1,1′-binaphthyl [III] and (2R,3R)-(-)-di-O-benzoyltartaric acid [(-)-DBT], and those of the isomers II were established on the basis of CD spectra of the phosphanes and their bisoxides. X-ray crystallog. studies of two cationic Rh1 complexes, [Rh{(S)-Cy-binap}(COD)]ClO4 [(S)-IV] and [Rh{(S)-H8-binap}(COD)]ClO4[(S)-V], revealed that complex (S)-IV possesses a disym. structure, while complex (S)-V has a pseudo-C2-symmetry and shows a significantly large dihedral angle between the two Ph rings [80.3(4)°]. The potentially of ligand II for asym. catalysis was demonstrated in RuII-catalyzed stereoselective hydrogenations of Me 2-(benzamidomethyl)-3-oxobutanoate, (in up to 92% d.e. and 99% e.e.) and geraniol (in 98% optical purity).

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Crystal structure. 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Safety of (R)-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

Trost, Barry M’s team published research in Angewandte Chemie, International Edition in 2011 | 152140-65-3

Angewandte Chemie, International Edition published new progress about Allylic alkylation (decarboxylative, stereoselective). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, COA of Formula: C54H42N2O2P2.

Trost, Barry M.; Schaeffner, Benjamin; Osipov, Maksim; Wilton, Donna A. A. published the artcile< Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect>, COA of Formula: C54H42N2O2P2, the main research area is stereoselective decarboxylative allylic alkylation keto ester palladium catalyst.

The palladium-catalyzed decarboxylative asym. allylic alkylation of β-keto esters is reported. This reaction was applied to the synthesis of (-)-ranirestat. It was expanded to β-keto esters by using allyl chloroformate to form allyl enol carbonates in situ. Two sets of reaction conditions were developed to fine-tune the enantioselectivity.

Angewandte Chemie, International Edition published new progress about Allylic alkylation (decarboxylative, stereoselective). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, COA of Formula: C54H42N2O2P2.

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

Li, Guanlin’s team published research in Chemistry – A European Journal in 2022 | 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.Category: chiral-phosphine-ligands

In 2022,Li, Guanlin; Zhao, Ling; Luo, Yicong; Peng, Youbin; Xu, Kai; Huo, Xiaohong; Zhang, Wanbin published an article in Chemistry – A European Journal. The title of the article was 《Stereodivergent Desymmetrization of Simple Dicarboxylates via Branch-Selective Pd/Cu Catalyzed Allylic Substitution》.Category: chiral-phosphine-ligands The author mentioned the following in the article:

Asym. desymmetrization has been demonstrated to be a powerful strategy for building stereocenters in asym. synthesis. Herein, a Pd/Cu catalyzed asym. desymmetrization reaction with a simple geminal dicarboxylate is reported. A wide scope of imino esters bearing an aryl or heteroaromatic group were compatible with this bimetallic catalytic system. The reactions proceeded smoothly, giving the desired products in good yields with high to excellent regio-, diastereo-, and enantioselectivity (up to 20 : 1 branched:linear, >20 : 1 dr, >99% ee). Notably, the reaction favored branched selectivity, which is unusual for the Pd-catalyzed allylic alkylation reaction. In addition, the standard product could be easily transformed to other valuable mols. such as chiral allylic alcs., carbamates, and organic boron compounds Furthermore, DFT calculations were conducted to explain the origin of the branched selectivity. 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) 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.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Porwanski, Stanislaw’s team published research in Carbohydrate Research in 2014 | CAS: 960128-64-7

(R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas:960128-64-7) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Computed Properties of C22H22NP This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Porwanski, Stanislaw published an article in Carbohydrate Research. The title of the article was 《New ureas containing glycosyl and diphenylphosphinyl scaffolds: synthesis and the first attempts to use them in asymmetric synthesis》.Computed Properties of C22H22NP The author mentioned the following in the article:

Chiral ureas containing glycosyl and diphenylphosphinyl scaffolds, e.g. I, were found to be an effective organocatalyst. They were synthesized in high yields by a one-pot tandem Staudinger/aza-Wittig coupling reaction. The first attempts of using them in asym. synthesis are presented. Yields of the Morita-Baylis-Hillman reaction were moderate with an enantiomeric excess of up to 80%. In the part of experimental materials, we found many familiar compounds, such as (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas: 960128-64-7Computed Properties of C22H22NP)

(R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas:960128-64-7) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Computed Properties of C22H22NP This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Jiao, Yunzhe’s team published research in Catalysis Science & Technology in 2017 | CAS: 210169-54-3

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes, stereoselective preparation of homoallylic alcohols via Ir-catalyzed stereoselective transfer hydrogenative crotylation of an allylic acetate with alcohols or aldehydesProduct Details of 210169-54-3

In 2017,Jiao, Yunzhe; Torne, Marta Serrano; Gracia, Jose; Niemantsverdriet, J. W.; van Leeuwen, Piet W. N. M. published 《Ligand effects in rhodium-catalyzed hydroformylation with bisphosphines: steric or electronic?》.Catalysis Science & Technology published the findings.Product Details of 210169-54-3 The information in the text is summarized as follows:

Twelve com. available bisphosphine ligands were evaluated in rhodium-catalyzed hydroformylation reactions. All ligands exhibited high chemoselectivities for aldehyde formation. The highest enantioselectivity (53% ee) of styrene hydroformylation was achieved with (S)-BTFM-Garphos (L7) substituted with electron withdrawing substituents. High pressure NMR (HP-NMR) spectroscopy and in situ high pressure IR spectroscopy (HP-IR) were used to study the resting states of the catalyst species in the reactions. The ligand effect on the structures of the observable species was examined Both electronic and steric factors were considered to contribute to the performance of the various ligands. Decreasing the phosphine basicity increased the enantioselectivity, while in the systems studied here the steric character plays a less important role than the electronic features in achieving good regioselectivities. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Product Details of 210169-54-3)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes, stereoselective preparation of homoallylic alcohols via Ir-catalyzed stereoselective transfer hydrogenative crotylation of an allylic acetate with alcohols or aldehydesProduct Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Xia, Yun-Tao’s team published research in Catalysis Science & Technology in 2017 | 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.SDS of cas: 210169-54-3

In 2017,Xia, Yun-Tao; Ma, Jing; Wang, Xiao-Dong; Yang, Lei; Wu, Lei published 《Enantioselective hydrogenation of N-heteroaromatics catalyzed by chiral diphosphine modified binaphthyl palladium nanoparticles》.Catalysis Science & Technology published the findings.SDS of cas: 210169-54-3 The information in the text is summarized as follows:

The first application of binaphthyl-stabilized palladium nanoparticles (Bin-PdNPs) with chiral modifiers in asym. hydrogenation of N-heteroaromatics was revealed. With an appropriate ratio of R-BINAP/Bin-PdNPs used, the pre-prepared chiral nanocatalyst achieved asym. hydrogenations of 2-substituted quinolines with good to excellent yields and moderate enantioselectivities, which showed superior catalytic properties to the R-BINAP/Pd complex. Moreover, this protocol was also applicable to 2-substituted indoles. The experimental process involved the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3SDS of 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.SDS of cas: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

He, Cheng-Yu’s team published research in Advanced Synthesis & Catalysis in 2020 | 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. 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. Product Details of 256390-47-3

《Copper-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Dienes》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to He, Cheng-Yu; Li, Qing-Hua; Wang, Xin; Wang, Feng; Tian, Ping; Lin, Guo-Qiang. Product Details of 256390-47-3 The article mentions the following:

Due to the low reactivity of 1,6-dienes and the challenge of selectively differentiating such two olefins, the development of metal-catalyzed asym. cyclization of 1,6-dienes remains largely underdeveloped. Herein, the authors describe the 1st Cu(I)-catalyzed asym. borylative cyclization of cyclohexadienone-tethered terminal alkenes (1,6-dienes) via a tandem process: the regioselective borocupration of the electron-rich terminal alkene and subsequent conjugate addition of stereospecific secondary alkyl-Cu(I) to the electron-deficient cyclohexadienone, affording enantioenriched bicyclic skeletons bearing three contiguous stereocenters in all cis-form. Meanwhile, this mild catalytic protocol is generally compatible with a wide range of functional groups, which allows further facile conversion of the cyclization products.(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Product Details of 256390-47-3) was used in this study.

(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. 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. Product Details of 256390-47-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis