Tag: 582.61

Diastereoselective synthesis of an argatroban intermediate, ethyl (2R,4R)-4-methylpipecolate, by means of a Mandyphos/rhodium complex-catalyzed hydrogenation was written by Ferraboschi, Patrizia;De Mieri, Maria;Grisenti, Paride;Lotz, Matthias;Nettekoven, Ulrike. And the article was included in Tetrahedron: Asymmetry in 2011.Reference of 133545-16-1 This article mentions the following:

The synthetic antithrombotic argatroban is a dipeptide between the nonproteinogenic (2R,4R)-4-methyl-2-piperidine carboxylic acid and L-arginine, in turn bonded to a methyltetrahydroquinoline sulfonyl group. An extensive screening of transition metal-based complexes with different ligands was performed in order to identify the best catalyst for the diastereoselective hydrogenation of a suitable 4,5-dehydropiperidine precursor aimed toward a synthesis of the (2R,4R)-4-Me piperidine moiety. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Reference of 133545-16-1).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Reference of 133545-16-1

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rhodium-Catalyzed Highly Diastereo- and Enantioselective Synthesis of a Configurationally Stable S-Shaped Double Helicene-Like Molecule was written by Kinoshita, Suzuka;Yamano, Ryota;Shibata, Yu;Tanaka, Yusuke;Hanada, Kyoichi;Matsumoto, Takashi;Miyamoto, Kazunori;Muranaka, Atsuya;Uchiyama, Masanobu;Tanaka, Ken. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) This article mentions the following:

An S-shaped double helicene-like mol. (>99% ee), possessing stable helical chirality, has been synthesized by the rhodium(I)/difluorphos complex-catalyzed highly diastereo- and enantioselective intramol. double [2+2+2] cycloaddition of a 2-naphthol- and benzene-linked hexayne. The collision between two terminal naphthalene rings destabilizes the helical chirality of the S-shaped double helicene-like mol., but the introduction of two addnl. fused benzene rings significantly increases the configurational stability. Thus, no epimerization and racemization were observed even at 100°C. The enantiopure S-shaped double helicene-like mol. forms a trimer through the multiple C-H…π and C-H…O interactions in the solid-state. The trimers stack to form columnar packing structures, in which neighboring stacks have opposite dipole directions. The accumulation of helical structures in the same direction in the S-shaped double helicene-like mol. enhanced the chiroptical properties. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Recommanded Product: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Recommanded Product: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cyclization of 1,6-Enynes with Aliphatic and Aromatic Alkenes was written by Ueda, Hiroki;Masutomi, Koji;Shibata, Yu;Tanaka, Ken. And the article was included in Organic Letters in 2017.Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) This article mentions the following:

It has been established that a cationic rhodium(I)/(R)-MeO-BIPHEP complex catalyzes the asym. [2 + 2 + 2] cyclization of 1,6-enynes with aliphatic and aromatic alkenes to produce chiral cyclic dienes through β-hydride elimination from rhodacycle intermediates. Thus, obtained chiral cyclic dienes could be converted to chiral spirocompounds without racemization. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric cyclocarbonylation of 1,6-enynes with cobalt catalysts was written by Schmid, Thomas M.;Consiglio, Giambattista. And the article was included in Tetrahedron: Asymmetry in 2004.Category: chiral-phosphine-ligands This article mentions the following:

Octacarbonyldicobalt or Co(II) salts in the presence of (R)-(6,6′-dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine) were active and highly enantioselective catalyst for the cyclocarbonylation of enynes such as 4,4-bis(carboethoxy)hex-6-en-1-yne. The reactivity of both catalytic systems towards cyclocarbonylation increased when the CO pressure was increased. However, when a stoichiometric amount of ligand was used, with respect to the catalyst, the enantioselectivity decreased, but increased again as the ligand-to-Co molar ratio increased. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Category: chiral-phosphine-ligands).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Ir(I)-catalyzed enantioselective hydrogenolysis of 3-aryl-3-hydroxyisoindolin-1-ones was written by Ge, Chen;Liang, Ren-Xiao;Liu, Ren-Rong;Xiang, Bin;Jia, Yi-Xia. And the article was included in Tetrahedron Letters in 2017.Reference of 133545-16-1 This article mentions the following:

An enantioselective hydrogenolysis of 3-aryl-3-hydroxyisoindolin-1-ones under H₂ was developed by using Ir(I)/(R)-MeO-Biphep complex as a catalyst. Cyclic diaryl methylamides were obtained in moderate to excellent yields and up to 92% ee. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Reference of 133545-16-1).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Reference of 133545-16-1

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Practical Synthesis of MDM2 Antagonist RG7388. Part 1: A Cu(II)-Catalyzed Asymmetric [3 + 2] Cycloaddition was written by Shu, Lianhe;Gu, Chen;Fishlock, Dan;Li, Zizhong. And the article was included in Organic Process Research & Development in 2016.Computed Properties of C38H32O2P2 This article mentions the following:

An efficient asym. synthesis of MDM2 antagonist RG7388 (I) is reported. The highly functionalized chiral pyrrolidine carboxamate was assembled via a Cu(OAc)₂/(R)-BINAP catalyzed asym. [3+2] cycloaddition, which gave the exo and endo adducts in a ratio of 10:1, with high enantiomeric excess for the exo isomer. A one pot hydrolysis and retro-Mannich/Mannich isomerization of the cycloaddition adducts in the presence of aqueous sodium hydroxide afforded RG7388 in high chem. and enantiomeric purities and 69% overall yield. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Computed Properties of C38H32O2P2).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Computed Properties of C38H32O2P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rapid virtual screening of enantioselective catalysts using CatVS was written by Rosales, Anthony R.;Wahlers, Jessica;Lime, Elaine;Meadows, Rebecca E.;Leslie, Kevin W.;Savin, Rhona;Bell, Fiona;Hansen, Eric;Helquist, Paul;Munday, Rachel H.;Wiest, Olaf;Norrby, Per-Ola. And the article was included in Nature Catalysis in 2019.Electric Literature of C38H32O2P2 This article mentions the following:

The development of computational tools to support organic synthesis, including the prediction of reaction pathways, optimization and selectivity, is a topic of intense current interest. Transition state force fields, derived by the quantum-guided mol. mechanics method, rapidly calculate the stereoselectivity of organic reactions accurately enough to allow predictive virtual screening. Here we describe CatVS, an automated tool for the virtual screening of substrate and ligand libraries for asym. catalysis within hours. It is shown for the OsO₄-catalyzed cis-dihydroxylation that the results from the automated set-up are indistinguishable from a manual substrate screen. Predictive computational ligand selection is demonstrated in the virtual ligand screen of a library of diphosphine ligands for the rhodium-catalyzed asym. hydrogenation of enamides. Subsequent exptl. testing verified that the most selective substrate-ligand combinations are successfully identified by the virtual screen. CatVS is therefore a promising tool to increase the efficiency of high-throughput experimentation. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Electric Literature of C38H32O2P2).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Electric Literature of C38H32O2P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

An efficient copper-aluminum hydrotalcite catalyst for asymmetric hydrosilylation of ketones at room temperature. [Erratum to document cited in CA149:246243] was written by Kantam, M. Lakshmi;Laha, Soumi;Yadav, Jagjit;Likhar, Pravin R.;Sreedhar, B.;Jha, Shailendra;Bhargava, Suresh;Udayakiran, M.;Jagadeesh, B.. And the article was included in Organic Letters in 2008.Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) This article mentions the following:

The Supporting Information Section contained errors in the optical rotation, concentration, H NMR chem. shift values, C NMR chem. shift values, HPLC retention times, and HPLC spectra. The corrected version of the Supporting Information is available online. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Catalytic Enantioselective Synthesis of γ-Lactams with β-Quaternary Centers via Merging of C-C Activation and Sulfonyl Radical Migration was written by Yu, Xuan;Zhang, Zining;Dong, Guangbin. And the article was included in Journal of the American Chemical Society in 2022.Application of 133545-16-1 This article mentions the following:

To expand the repertoire of C-C activation, here the discovery of a Rh-catalyzed enantioselective C-C activation involving migration of a sulfonyl radical were described. This reaction directly transforms cyclobutanones containing a sulfonamide-tethered 1,3-diene moiety into γ-lactams containing a β-quaternary center with excellent enantioselectivity. This unusual process involved cleavage of C-C and N-S bonds and subsequent formation of C-N and C-S bonds. The reaction also exhibited broad functional group tolerance and a good substrate scope. A combined exptl. and computational mechanistic study suggested that the reaction goes through a Rh(I)-mediated oxidative addition into the cyclobutanone C-C bond followed by a Rh(III)-triggered N-S bond homolysis and sulfonyl radical migration. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Application of 133545-16-1).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Application of 133545-16-1

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Synthesis of benzannulated spiroacetals using chiral gold-phosphine complexes and chiral anions was written by Quach, Rachelle;Furkert, Daniel P.;Brimble, Margaret A.. And the article was included in Tetrahedron Letters in 2013.Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) This article mentions the following:

The development of an asym. gold-catalyzed dihydroalkoxylation strategy for the synthesis of the 3’H-spiro[chroman-2,1′-isobenzofuran] spiroketal ring system I is described. Spiroacetal I was generated in up to 87:13 enantiomeric ratio using chiral gold-phosphine complexes and chiral silver phosphate Ag(S)-TRIP. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Quality Control of (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis