Day: October 13, 2022

Formula: C50H56O14P2On November 12, 2014 ,《Copper-Catalyzed Diastereo- and Enantioselective Desymmetrization of Cyclopropenes: Synthesis of Cyclopropylboronates》 appeared in Journal of the American Chemical Society. The author of the article were Parra, Alejandro; Amenos, Laura; Guisan-Ceinos, Manuel; Lopez, Aurora; Garcia Ruano, Jose Luis; Tortosa, Mariola. The article conveys some information:

A novel Cu-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes to afford nonracemic cyclopropylboronates is described. Trapping the cyclopropylcopper intermediate with electrophilic amines allows for the synthesis of cyclopropylaminoboronic esters and demonstrates the potential of the approach for the synthesis of functionalized cyclopropanes. After reading the article, we found that the author used (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Formula: C50H56O14P2)

(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. Formula: C50H56O14P2 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

Reference of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferroceneOn November 29, 2013 ,《Cobalt Precursors for High-Throughput Discovery of Base Metal Asymmetric Alkene Hydrogenation Catalysts》 appeared in Science (Washington, DC, United States). The author of the article were Friedfeld, Max R.; Shevlin, Michael; Hoyt, Jordan M.; Krska, Shane W.; Tudge, Matthew T.; Chirik, Paul J.. The article conveys some information:

Asym. hydrogenation of alkenes is one of the most widely used methods for the preparation of single enantiomer compounds, especially in the pharmaceutical and agrochem. industries. For more than four decades, precious metal complexes containing rhodium, iridium, and ruthenium have been predominantly used as catalysts. Here, we report rapid evaluation of libraries of chiral phosphine ligands with a set of simple cobalt precursors. From these studies, base metal precatalysts have been discovered for the hydrogenation of functionalized and unfunctionalized olefins with high enantiomeric excesses, demonstrating the potential utility of more earth-abundant metals in asym. hydrogenation. In the part of experimental materials, we found many familiar compounds, such as (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene(cas: 1221746-56-0Reference of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene)

(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene(cas: 1221746-56-0) 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. Reference of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Brewitz, Lennart; Arteaga, Fernando Arteaga; Yin, Liang; Alagiri, Kaliyamoorthy; Kumagai, Naoya; Shibasaki, Masakatsu published their research in Journal of the American Chemical Society on December 23 ,2015. The article was titled 《Direct Catalytic Asymmetric Mannich-Type Reaction of α- and β-Fluorinated Amides》.Computed Properties of C43H63FeNP2 The article contains the following contents:

The last two decades have witnessed the emergence of direct enolization protocols providing atom-economical and operationally simple methods to use enolates for stereoselective C-C bond-forming reactions, eliminating the inherent drawback of the preformation of enolates using stoichiometric amounts of reagents. In its infancy, direct enolization relied heavily on the intrinsic acidity of the latent enolates, and the reaction scope was limited to readily enolizable ketones and aldehydes. Recent advances in this field enabled the exploitation of carboxylic acid derivatives for direct enolization, offering expeditious access to synthetically versatile chiral building blocks. Despite the growing demand for enantioenriched fluorine-containing small mols., α- and β-fluorinated carbonyl compounds have been neglected in direct enolization chem. because of the competing and dominating defluorination pathway. Herein we present a comprehensive study on direct and highly stereoselective Mannich-type reactions of α- and β-fluorine-functionalized 7-azaindoline amides that rely on a soft Lewis acid/hard Bronsted base cooperative catalytic system to guarantee an efficient enolization while suppressing undesired defluorination. This protocol contributes to provide a series of fluorinated analogs of enantioenriched β-amino acids for medicinal chem.(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Computed Properties of C43H63FeNP2) was used in this study.

(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. Computed Properties of C43H63FeNP2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

SDS of cas: 210169-54-3In 2016 ,《Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination》 appeared in Journal of the American Chemical Society. The author of the article were Garza, Victoria J.; Krische, Michael J.. The article conveys some information:

Chiral iridium complexes modified by SEGPHOS catalyze the 2-propanol-mediated reductive coupling of branched allylic acetates with formaldehyde to form primary homoallylic alcs. with excellent control of regio- and enantioselectivity. These processes, which rely on enantiotopic π-facial discrimination of σ-allyliridium intermediates, represent the first examples of enantioselective formaldehyde C-C coupling beyond aldol addition 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: 210169-54-3SDS 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

《Development of a Large-Scale Synthetic Route to Manufacture (-)-Huperzine A》 was written by Tudhope, Stephen R.; Bellamy, Julie A.; Ball, Anthony; Rajasekar, Dewakar; Azadi-Ardakani, Manouchehr; Meera, Harihara Subramanian; Gnanadeepam, Jesudoss Mercy; Saiganesh, Ramanathan; Gibson, Frank; He, Linli; Behrens, Carl H.; Underiner, Gail; Marfurt, Judith; Favre, Nathalie. Synthetic Route of C43H63FeNP2 And the article was included in Organic Process Research & Development on April 20 ,2012. The article conveys some information:

A safe, practical and scalable process for manufacture of (-)-huperzine A has been developed and scaled up to manufacture several hundred grams of (-)-huperzine A with chem. and optical purity of >99%. The process consists of 11 chem. stages starting from com. available materials with only nine isolation steps and no chromatog. purification This process provides a reliable and cost-effective source of synthetic (-)-huperzine A and its derivatives for pharmaceutical and nutraceutical markets. A hazard evaluation assessment indicated that the safety margin for DPPA thermal decomposition onset is sufficient for conducting reaction at intended scale. In the experiment, the researchers used (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Synthetic Route of C43H63FeNP2)

(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. Synthetic Route of C43H63FeNP2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Tindall, Daniel J.; Mader, Steffen; Kindler, Alois; Rominger, Frank; Hashmi, A. Stephen K.; Schaub, Thomas published an article on January 11 ,2021. The article was titled 《Selective and Scalable Synthesis of Sugar Alcohols by Homogeneous Asymmetric Hydrogenation of Unprotected Ketoses》, and you may find the article in Angewandte Chemie, International Edition.Quality Control of (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine The information in the text is summarized as follows:

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. The experimental part of the paper was very detailed, including the reaction process of (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas: 960128-64-7Quality Control of (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine)

(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.Quality Control of (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-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

In 2015,Angewandte Chemie, International Edition included an article by Pritzius, Adrian B.; Breit, Bernhard. Product Details of 256390-47-3. The article was titled 《Asymmetric Rhodium-Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones》. The information in the text is summarized as follows:

A highly regio- and enantioselective hydrothiolation of terminal allenes, a reaction which fulfills the criteria of atom economy, is reported. Applying two chiral rhodium catalyst systems, a wide variety of thiols and allenes could be coupled. Oxidation gave access to the corresponding allylic sulfones in essentially enantiomerically pure form. The reaction tolerates a variety of functional groups and labeling experiments gave first insights into the reaction mechanism of this new methodol. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Product Details 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. Product Details 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

In 2019,Bulletin of the Chemical Society of Japan included an article by Tsukamoto, Hirokazu; Kawase, Ayumu; Omura, Hirotaka; Doi, Takayuki. Application of 210169-54-3. The article was titled 《Key Factors for High Diastereo- and Enantioselectivity of Umpolung Cyclizations of Aldehyde-Containing Allylpalladium Intermediates》. The information in the text is summarized as follows:

Two palladium/chiral diphosphine-catalyzed umpolung cyclizations of aldehyde-containing allylic acetates and allenes with arylboronic acid are fully investigated to establish key factors in their high stereoselectivities. Both cyclization reactions afford cis-disubstituted pyrrolidine and THF. These occur in high diastereo- and enantioselectivities through a common cationic (Z)-η1-allylpalladium, toward which a ring strain generated in the cyclization step leading to trans-isomers biases the equilibrium through η3-η1-η3-complex in the former cyclization. Varied diastereoselectivities were observed in the formation of five-membered carbocycles and six-membered heterocycles. These reflect release of a ring strain generated in the cyclization step leading to trans-isomers and a different distribution of the (Z)- and the (E)-η1-allylpalladium intermediates generated by the oxidative addition of allylic acetates to Pd(0) or carbopalladation of allenes, resp. A sterically demanding substituent at the center of the allyl moiety is necessary for high diastereo- and enantioselectivity. The enantioselectivity of the former cyclization was lowered by the presence of organometallic reductants or reagents, possibly causing the formation of neutral η1-allylpalladium species. We used a chiral allylic acetate containing (E)-deuterium-labeled alkene to demonstrate that the electrophilic attack of the aldehyde to the allyl ligand occurred on the side where the palladium existed, consistent with the Zimmerman-Traxler transition state. In the experiment, the researchers used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Application of 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.Application of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Enantioselective total synthesis of furofuran lignans via Pd-catalyzed asymmetric allylic cycloaddition of vinylethylene carbonates with 2-nitroacrylates》 was written by Zhao, Can; Khan, Ijaz; Zhang, Yong Jian. Recommanded Product: (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020. The article conveys some information:

Herein, a practical and efficient approach to tetrahydrofurans with three-stereocenters has been developed through Pd-catalyzed asym. allylic cycloaddition of vinylethylene carbonates (VECs) with 2-nitroacrylates under mild conditions. By using this asym. catalytic reaction as a key step, several furofuran lignans with stereodivergency have been effectively synthesized through 5- or 6-step sequences from readily available starting materials. 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: (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) 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 aldehydesRecommanded Product: (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Ye, Xiang-Yu; Liang, Zhi-Qin; Jin, Cong; Lang, Qi-Wei; Chen, Gen-Qiang; Zhang, Xumu published an article in 2021. The article was titled 《Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin via iridium-catalyzed asymmetric hydrogenation》, and you may find the article in Chemical Communications (Cambridge, United Kingdom).Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The information in the text is summarized as follows:

Phosphine-oxazoline (PHOX) ligands are a very important class of privileged ligands in asym. catalysis. A series of highly rigid oxa-spiro phosphine-oxazoline (O-SIPHOX) ligands based on O-SPINOL was synthesized efficiently, and their iridium complexes were synthesized by coordination of the O-SIPHOX ligands to [Ir(cod)Cl]2 in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asym. hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol. 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