Day: October 17, 2022

Quality Control of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine]On May 7, 2021 ,《Copper-Catalyzed Asymmetric Reductions of Aryl/Heteroaryl Ketones under Mild Aqueous Micellar Conditions》 appeared in Organic Letters. The author of the article were Fialho, David M.; Etemadi-Davan, Elham; Langner, Olivia C.; Takale, Balaram S.; Gadakh, Amol; Sambasivam, Ganesh; Lipshutz, Bruce H.. The article conveys some information:

Enantioselective syntheses of nonracemic secondary alcs. have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)2.H2O/(R)-3,4,5-MeO-MeO-BIPHEP) reduction of aryl/heteroaryl ketones. This methodol. serves as a green protocol to access enantio-enriched alcs. under mild conditions (0-22°C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alc. products are formed in good to excellent yields with ee values greater than 90%. In the experiment, the researchers used (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Quality Control of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine])

(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. Quality Control of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine]

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Asymmetric Hydrogenation of 2-Aryl-3-phthalimidopyridinium Salts: Synthesis of Piperidine Derivatives with Two Contiguous Stereocenters》 was published in Organic Letters in 2020. These research results belong to Zheng, Long-Sheng; Wang, Fangyuan; Ye, Xiang-Yu; Chen, Gen-Qiang; Zhang, Xumu. Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article mentions the following:

Asym. hydrogenation of 2-aryl-3-phthalimidopyridinium salts catalyzed by the Ir/SegPhos catalytic system was described, leading to the corresponding chiral piperidine derivatives bearing two contiguous chiral centers, with high levels of enantioselectivities and diastereoselectivities. A gram-scale experiment has demonstrated the utility of this approach. The phthaloyl group could be easily removed and then smoothly converted to key intermediate (+)-CP-99994 as one of the neurokinin 1 receptor antagonists.(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) 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.Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Mifleur, Alexis; Suisse, Isabelle; Mortreux, Andre; Sauthier, Mathieu published their research in Catalysis Letters in 2021. The article was titled 《Enantioselective Nickel Catalyzed Butadiene Hydroalkoxylation with Ethanol: from Experimental Results to Kinetics Parameters》.Recommanded Product: 210169-54-3 The article contains the following contents:

The enantioselective hydroalkoxylation of butadiene with ethanol has been performed in the presence of nickel-based catalysts and chiral diphosphine ligands. Ee’s up to 77% could be obtained from the use of atropoisomeric chiral ligands such as Segphos. The kinetics parameters of the reaction were determined using a qual. kinetic model to better explain the l/b isomerization and racemization processes observed for long reaction times. The experimental part of the paper was very detailed, including the reaction process of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Recommanded Product: 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.Recommanded Product: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Domino Asymmetric Conjugate Addition-Conjugate Addition》 was written by Germain, Nicolas; Schlaefli, Doriane; Chellat, Mathieu; Rosset, Stephane; Alexakis, Alexandre. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene And the article was included in Organic Letters on April 4 ,2014. The article conveys some information:

In the presence of copper catalysts and nonracemic phosphoramidite, imidazolium, or aminoferrocenylphosphine ligands, ethylmagnesium bromide, trimethylaluminum, and dimethyl- and diethylzinc underwent enantioselective and diastereoselective conjugate addition reactions to cyclopentenones, cyclohexenones, and cycloheptenones followed by trapping with either nitroalkenes or 1,1-bis(phenylsulfonyl)ethylene to give oxoalkyl cycloalkanones in 63-85% yields, 57:43-97:3 dr, and in 86->99.5% ee; the oxoalkyl cycloalkanones were converted by various methods to indenones, a hydrazulenone, a tetrahydrobenzofuran and a tetrahydroindole, and an octahydronaphthalene. In the experiment, the researchers used many compounds, for example, (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene)

(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3) 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. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Novel N,N,P-Tridentate Ligands for the Highly Enantioselective Copper-Catalyzed 1,4-Addition of Dialkylzincs to Enones》 was written by Kawamura, Kenjiro; Fukuzawa, Hitomi; Hayashi, Masahiko. Safety of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine And the article was included in Organic Letters on August 21 ,2008. The article conveys some information:

Use of 0.25 mol % of the N,N,P-tridentate ligands (S)-QuCH:NCHRCH2PPh2 (Qu = 2-quinolyl) and 0.1 mol % of Cu(OTf)2 enabled the enantioselective 1,4-addition of dialkylzincs to cyclic enones to produce 1,4-adducts in up to 99% ee.(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Safety of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine) was used in this study.

(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.Safety 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

《Palladium-catalysed intramolecular asymmetric cyclohydroaryloxycarbonylation of 2-allylphenol derivatives. Synthesis of chiral lactones via cyclocarbonylation》 was published in Molecular Catalysis in 2020. These research results belong to Abu Seni, Anas; Kollar, Laszlo; Pongracz, Peter. HPLC of Formula: 210169-54-3 The article mentions the following:

Homogeneous catalytic hydroaryloxycarbonylation of 2-allylphenol derivatives I (R1 = H, CH3, OCH3, CHO; R2 = H, COCH3) was performed using palladium complexes toward the corresponding lactones II, III, IV. Reactions were conducted under carbon monoxide atm. in the absence of hydrogen gas. Palladium catalyst was generated in situ, using various phosphine ligands e.g., (4S,5S)-4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane and precursors as Pd(OAc)2, PdCl2, PdCl2(PhCN)2, etc. in the presence of acid additives as HCl, HCOOH, TsOH, etc. In general, chiral 6- III and achiral 7-membered lactones IV were formed dominantly, only trace amounts of the 5-membered lactone II can be identified. Moderate or good enantioselectivity can be achieved using chiral ligands regarding the 6-membered chromanone derivatives III. The regioselectivity of the reaction is particularly effected by catalyst composition and acid co-catalysts and found to be insensitive for substrate substitution. The results came from multiple reactions, including the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3HPLC of Formula: 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 aldehydesHPLC of Formula: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Modular Fragment Synthesis and Bioinformatic Analysis Propose a Revised Vancoresmycin Stereoconfiguration》 was written by Spindler, Stefanie; Wingen, Lukas M.; Schoenenbroicher, Max; Seul, Maximilian; Adamek, Martina; Essig, Sebastian; Kurz, Michael; Ziemert, Nadine; Menche, Dirk. COA of Formula: C38H28O4P2This research focused onvancoresmycin fragment preparation configuration revision. The article conveys some information:

Elaborate fragments of the proposed stereostructure of the complex polyketide antibiotic vancoresmycin have been synthesized in a stereoselective fashion based on a modular and convergent approach. Significant NMR differences in one of these subunits compared with the natural product question the proposed stereoconfiguration. Consequently, an extensive bioinformatics anal. of the biosynthetic gene cluster was carried out, leading to a revised stereoconfigurational proposal for this highly potent antibiotic. The results came from multiple reactions, including the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3COA of Formula: C38H28O4P2)

(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.COA of Formula: C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Arai, Takayoshi; Sato, Katsuya; Nakamura, Ayu; Makino, Hiroki; Masu, Hyuma published their research in Scientific Reports on December 31 ,2018. The article was titled 《Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis》.Product Details of 286454-86-2 The article contains the following contents:

A phosphoiminoBINOL ligand was designed to form a dinuclear metal complex that could hold a malononitrile mol. The dinuclear bis(phosphoimino)binaphthoxy-Pd2(OAc)2 complex catalyzed a double Mannich reaction of N-Boc-imines with malononitrile to give chiral 1,3-diamines I (R = Ph, 2-MeC6H4, 2-NO2C6H4, etc.) with high enantioselectivity. The rational asym. catalyst, which smoothly introduces the first coupling product to the second coupling reaction while avoiding the reverse reaction, facilitates the over-reaction into a productive reaction process. After reading the article, we found that the author used (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Product Details of 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.Product Details 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.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

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)

(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.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《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