chiral-phosphine-ligands| Page 39 of 630 | Chiral phosphine ligands

Tan, Yun’s team published research in Advanced Synthesis & Catalysis in 2020 | 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.Application In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

《Water-Promoted Palladium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Alkoxysilanes》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to Tan, Yun; Yao, Yongqi; Yang, Wen; Lin, Qifu; Huang, Guobao; Tan, Minxiong; Chen, Shuqi; Chen, Donghan; Yang, Dingqiao. Application In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article mentions the following:

Water-promoted palladium-catalyzed asym. ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of alkoxysilanes was developed in a one-pot fashion, yielding cis-1,2-dihydronaphthalen-1-ols I [R1 = CH=CH2, Ph, 1-naphthyl, etc.; R2 = H, OMe; R3 = H, Me, Br, etc.; R4 = H, Me, F, etc.; R5 = H, OMe] in favorable yields (up to 98%) with gratifying enantioselectivities (up to 98% ee) under mild conditions. Furthermore, the cis-1,2-configuration of product was established by X-ray diffraction anal., and a possible mechanism for the present catalytic ring-opening reaction was also proposed. In the experiment, the researchers used many compounds, for example, (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Application In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Ebisu, Yasuhiro’s team published research in Tetrahedron: Asymmetry in 2012 | CAS: 286454-86-2

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Application of 286454-86-2 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.

Ebisu, Yasuhiro; Kawamura, Kenjiro; Hayashi, Masahiko published an article in Tetrahedron: Asymmetry. The title of the article was 《Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones using a novel N,N,P-Cu(II) complex》.Application of 286454-86-2 The author mentioned the following in the article:

Enantioselective copper-catalyzed 1,4-additions of dialkylzincs R2Zn (R = Et, Me) to enones I [X = (CH2)n, n = 0-2] and II (R1 = H, R2 = H, Me; R1 = MeO, NO2, F, R2 = H) were carried out in the presence of 1 mol % of Cu(OTf)2 and 2.5 mol % of an N,N,P-ligand possessing a tert-Bu group at the adjacent position of the nitrogen of pyridine to afford the corresponding 1,4-adducts III and IV, resp., in up to 98% ee. The results came from multiple reactions, including the reaction of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Application of 286454-86-2)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Yu, Chang-Bin’s team published research in Science China: Chemistry in 2020 | CAS: 210169-54-3

《Reversal of diastereoselectivity in palladium-arene interaction directed hydrogenative desymmetrization of 1,3-diketones》 was written by Yu, Chang-Bin; Wang, Heng-Ding; Song, Bo; Shen, Hong-Qiang; Fan, Hong-Jun; Zhou, Yong-Gui. Synthetic Route of C38H28O4P2 And the article was included in Science China: Chemistry in 2020. The article conveys some information:

Herein, an unprecedented trans reductive products were observed in palladium-catalyzed hydrogenative desymmetrization of cyclic and acyclic 1,3-diketones, providing the chiral trans β-hydroxy ketones with two adjacent stereocenters including one α-tertiary or quaternary stereocenter with high enantioselectivity and diastereoselectivity. Mechanistic studies and DFT calculations suggested that the rarely observed diastereoselectivity reversal is ascribed to the charge-charge interaction between the palladium and aromatic ring of the substrate, which could not only result in the reversal of the diastereoselectivity, but also improve the reactivity. The experimental process involved the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Synthetic Route of C38H28O4P2)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Liu, Xuan’s team published research in Organic Chemistry Frontiers in 2020 | 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.Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

《Catalytic enantioselective alkylation of 2-alkoxy-tetrahydrofurans》 was published in Organic Chemistry Frontiers in 2020. These research results belong to Liu, Xuan; Sun, Shaofa; Wang, Gang; Bai, Zhushuang; Pang, Jingxiang; Liu, Lei. Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article mentions the following:

Catalytic asym. addition to non-resonance-stabilized oxocarbenium ions has remained a formidable challenge. Herein, a nickel(II)-catalyzed asym. alkylation of non-resonance-stabilized, five-membered oxocarbenium ions generated in situ from 2-alkoxy tetrahydrofurans I (R = Et, n-Pn, Bn, t-Bu) with a broad range of carboxylic acid derivatives II (X = O, S; R1 = 4-fluorophenyl, naphthalen-1-yl, pent-1-en-1-yl, etc.) was disclosed. The reaction exhibits high efficiency, excellent enantioselectivity, and good functional group tolerance, and can be conducted on a large scale. Aside from five-membered oxocarbenium ions, six-membered 2-(pentyloxy)oxane and acyclic aliphatic species such as 1,1-dimethoxyhexane, Me 5,5-dimethoxyvalerate were also well tolerated with excellent enantiocontrol, thus providing a practical and robust method to access enantiopure α-alkyl substituted saturated ethers e.g., III. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Su, Hsin Y.’s team published research in Supramolecular Chemistry in 2019 | CAS: 286454-86-2

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine 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.

《Chiral phosphine ligand libraries based on the Bull-James three-component supramolecular assembly》 was written by Su, Hsin Y.; Gorelik, Daniel; Taylor, Mark S.. Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine And the article was included in Supramolecular Chemistry in 2019. The article conveys some information:

An approach to the synthesis of libraries of chiral phosphine ligands is described, using condensations of 2-formylarylboronic acids, diols or related compounds, and aminophosphines. The three-component nature of this condensation, along with the ready availability of the building blocks, enables the rapid generation of diverse structures. From a library of iminoboronate-derived phosphines, three ligands that gave 90% ee or greater in a benchmark palladium-catalyzed allylic substitution reaction were identified. Significant variation of selectivity as a function of the structure of each component was observed 11B NMR spectroscopy was used to evaluate the existence of B-N interactions in the free ligands as well as their Pd-derived complexes. A bidentate P,N-coordination mode was inferred for ligands that gave high enantioselectivity in the allylic substitution reaction. In the experiment, the researchers used many compounds, for example, (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine 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

Wang, Hong-Yu’s team published research in Nature Communications in 2016 | CAS: 286454-86-2

Wang, Hong-Yu; Zheng, Chang-Wu; Chai, Zhuo; Zhang, Jia-Xing; Zhao, Gang published an article in Nature Communications. The title of the article was 《Asymmetric cyanation of imines via dipeptide-derived organophosphine dual-reagent catalysis》.Application of 286454-86-2 The author mentioned the following in the article:

Reported herein is an application of enantioselective phosphine organocatalysis for asym. Strecker-type reactions, enabled by a dual-reagent catalyst system in which the key organophosphorus zwitterion intermediate, generated in situ by mixing a chiral dipeptide-derived multifunctional organophosphine with Me acrylate, e.g., I, is used as a highly efficient chiral Lewis base catalyst. The high efficiency of this catalytic system is demonstrated in the asym. cyanation of isatin-derived ketimines and azomethine aldimines as well as in the kinetic resolution of racemic 3-substituted azomethines. Mechanistic studies provide exptl. evidence for the intermediacy of the putative zwitterion and its role as a catalytically active Lewis base. In the part of experimental materials, we found many familiar compounds, such as (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Application of 286454-86-2)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

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.

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).

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

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.