Tag: 600-700

The author of 《Palladium-Catalyzed Umpolung Type-II Cyclization of Allylic Carbonate-Aldehydes Leading to 3-methylenecycloalkanol Derivatives》 were Tsukamoto, Hirokazu; Kawase, Ayumu; Doi, Takayuki. And the article was published in Advanced Synthesis & Catalysis in 2019. HPLC of Formula: 210169-54-3 The author mentioned the following in the article:

Palladium-catalyzed umpolung type-II cyclization of allylic carbonate-aldehydes leading to 3-methylenecycloalkanol derivatives was developed [e.g., I -> II (99%)]. The formate reductant was effective for the cyclization without causing a reduction of the η3-allylpalladium intermediate. One-pot decarboxylative allylation of aldehyde-containing malonate with 2-[(acetyloxy)methyl]-2-propenyl Me carbonate followed by the cyclization of the allyl acetate-aldehyde formed in situ was also achieved. The high diastereoselectivities observed in the cyclization of branched substrates indicates that a chair-chair transition state should be involved. Based on the presumed transition state, we could predict the enantioselectivity of the cyclization using SEGPHOS as a chiral diphosphine ligand and obtain optically active alcs. in up to 95:5 er.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3HPLC of Formula: 210169-54-3) was used in this study.

(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.HPLC of Formula: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2019,Journal of Organic Chemistry included an article by Chowdhury, Raghunath; Dubey, Akhil K.; Ghosh, Sunil K.. Product Details of 210169-54-3. The article was titled 《Ag(I)-Fesulphos-Catalyzed Enantioselective Synthesis of 3-Silylproline Derivatives》. The information in the text is summarized as follows:

An efficient catalytic asym. 1,3-dipolar cycloaddition of N-benzylidineiminoglycinate-derived azomethine ylides to β-silylmethylene malonates catalyzed by a Ag(I)-(1S)-1-[(1,1-dimethylethyl)thio]-2-(diphenylphosphino)ferrocene complex has been developed, affording fully substituted 3-silylproline derivatives with an all carbon quaternary center. The silylproline derivatives were obtained in moderate-to-good yields (up to 81%) in high diastereoselectivities and enantioselectivities (dr up to 95:5; er up to 96:4). Tamao-Fleming oxidation of selected 3-silylproline derivatives provided not only an efficient route but also the shortest route to 3-hydroxyproline derivatives, which are not accessible by direct 1,3-dipolar cycloadditions of azomethine ylide with frequently used arylidene/alkylidene malonates. The experimental process involved the reaction of (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) 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.Product Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2016,You, Cai; Wei, Biao; Li, Xiuxiu; Yang, Yusheng; Liu, Yue; Lv, Hui; Zhang, Xumu published 《Rhodium-Catalyzed Desymmetrization by Hydroformylation of Cyclopentenes: Synthesis of Chiral Carbocyclic Nucleosides》.Angewandte Chemie, International Edition published the findings.Application In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The information in the text is summarized as follows:

Excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (up to >99:1 d.r.) have been achieved in the desymmetrization of cyclopentenes by catalytic hydroformylation. This novel methodol. provides an efficient and concise synthetic route to chiral cyclopentane carboxaldehydes. The key intermediate, (1S,3S)-(3-hydroxymethyl)cyclopentanol, for the synthesis of carbocyclic-ddA was obtained in three steps. In the experiment, the researchers used (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)

(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 In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Low-pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes》 was written by Movahhed, Sohajl; Westphal, Julia; Dindaroglu, Mehmet; Falk, Anna; Schmalz, Hans-Guenther. Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleThis research focused onvinylarene ethene cobalt catalyst enantioselective regioselective hydrovinylation; alkenylarene preparation; C−C bond formation; alkenes; asymmetric catalysis; chirality; cobalt. The article conveys some information:

An efficient and practical protocol for the enantioselective cobalt-catalyzed hydrovinylation of vinylarenes with ethylene at low (1.2 bar) pressure was developed. As precatalysts, stable [L2CoCl2] complexes were employed that were activated in situ with Et2AlCl. A modular chiral TADDOL-derived phosphine-phosphite ligand was identified and that allowed the conversion of a broad spectrum of substrates including heterocyclic vinylarenes and vinylferrocene to smoothly afford the branched products with up to 99 % ee and virtually complete regioselectivity. Even polar functional groups such as OH, NH2, CN, and CO2R were tolerated. In the experiment, the researchers used many compounds, for example, (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Reference 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) 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 aldehydesReference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Cadart, Timothee; Necas, David; Kaiser, Reinhard P.; Favereau, Ludovic; Cisarova, Ivana; Gyepes, Robert; Hodacova, Jana; Kalikova, Kveta; Bednarova, Lucie; Crassous, Jeanne; Kotora, Martin published their research in Chemistry – A European Journal in 2021. The article was titled 《Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes》.Synthetic Route of C38H28O4P2 The article contains the following contents:

The enantioselective synthesis of chiral [7]-helical dispirodihydro[2,1-c]indenofluorenes (DSF-IFs) was achieved for the first time in good yields with high er values (er up to 99 : 1). The crucial step of the whole reaction sequence was the enantioselective intramol. [2+2+2] cycloaddition of tethered triynediols to indenofluorenediols, which was catalyzed by a Rh/SEGPHOS complex. Further transformations led to the corresponding DSF-IFs. The prepared helically chiral DSF-IFs combine circularly polarized luminescence (CPL) activity (glum=∼10-3) with exceptionally high fluorescence quantum yields (up to Φlum=0.97). In the part of experimental materials, we found many familiar compounds, such as (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Synthetic Route of C38H28O4P2)

(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.Synthetic Route of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2018,Bora, Pranjal P.; Sun, Gui-Jun; Zheng, Wei-Feng; Kang, Qiang published 《Rh/Lewis Acid Catalyzed Regio-, Diastereo- and Enantioselective Addition of 2-Acyl Imidazoles with Allenes》.Chinese Journal of Chemistry published the findings.Synthetic Route of C38H28O4P2 The information in the text is summarized as follows:

A highly regio-, diastereo- and enantioselective addition of 2-acyl imidazoles or 2-acyl pyridines with allenes promoted by Rh/Lewis acid synergistically catalytic system was described. This atom economic approach led to the formation of the branched allylic alkylated products including acyclic quaternary all-carbon stereogenic centers in good yields with good to excellent diastereo- and enantioselectivities. Kinetic studies revealed that the rate-determining step in this process was the oxidative addition of Rh(I) with C-H bond. The results came from multiple reactions, including the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Synthetic Route of 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.Synthetic Route of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Shi, Zhanglin; Shen, Chaoren; Dong, Kaiwu published an article in 2021. The article was titled 《Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones》, and you may find the article in Chemistry – A European Journal.Category: chiral-phosphine-ligands The information in the text is summarized as follows:

Palladium-catalyzed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed. In the part of experimental materials, we found many familiar compounds, such as (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

《Pd-Catalyzed asymmetric [5 + 2] cycloaddition of vinylethylene carbonates and cyclic imines: access to N-fused 1,3-oxazepines》 was written by Ahn, Hye-In; Park, Jong-Un; Xuan, Zi; Kim, Ju Hyun. SDS of cas: 210169-54-3 And the article was included in Organic & Biomolecular Chemistry in 2020. The article conveys some information:

A Pd-catalyzed asym. [5 + 2] cycloaddition reaction was developed for the synthesis of N-fused 1,3-oxazepines using vinylethylene carbonates and sulfamate-derived cyclic imines. Under mild reaction conditions, a series of optically active N-fused 1,3-oxazepines were synthesized in good yields (up to 89%) and enantioselectivities (up to 90 : 10 er), indicating this method as a straightforward approach to enantiomerically enriched 1,3-oxazepine derivatives The synthetic utility of the presented reaction was further demonstrated by the successful transformation of the resulting 1,3-oxazepines to useful polycyclic N-fused 1,3-oxazepanes. In the experiment, the researchers used (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) 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 aldehydesSDS of cas: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Recommanded Product: 210169-54-3In 2019 ,《Enantioselective Synthesis of Nine- to Eleven-Membered Cyclic Polyphenylenes Containing Heteroatoms by Catalytic Intramolecular [2+2+2] Cycloaddition》 was published in Asian Journal of Organic Chemistry. The article was written by Shibata, Takanori; Fusamae, Toru; Takano, Hideaki; Sugimura, Natsuhiko; Kanyiva, Kyalo Stephen. The article contains the following contents:

Rh-catalyzed enantioselective intramol. reactions of triynes consisting of 1,6-diyne and 1,10-diyne moieties tethered by sulfur or oxygen and ortho-phenylene moieties proceeded to give chiral tetrabenzoheteronines possessing a nine-membered ring system as [2+2+2] cycloadducts. In the reaction of triynes consisting of 1,6-diyne and 1,11-diyne moieties, sulfur-tethered substrates gave chiral metacyclophanes with an eleven-membered ring system, whereas an oxygen- and sulfur-tethered substrate afforded a tetrabenzo-1,4-oxathiecine with a ten-membered ring system. The mechanisms of the different reaction pathways depending on the heteroatom of the ether were discussed. The results came from multiple reactions, including the reaction 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) 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: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

COA of Formula: C38H28O4P2In 2016 ,《Synthesis of β-Boryl-α-Aminosilanes by Copper-Catalyzed Aminoboration of Vinylsilanes》 was published in Angewandte Chemie, International Edition. The article was written by Kato, Kodai; Hirano, Koji; Miura, Masahiro. The article contains the following contents:

A Cu-catalyzed regioselective and stereospecific aminoboration of vinylsilanes with bis(pinacolato)diboron (pinB-Bpin) and hydroxylamines was developed. In the presence of a CuCl/MeO-dppbz catalyst, the boryl group and amino group are incorporated at the β position and α position, resp., and the corresponding β-boryl-α-aminosilanes were obtained with good diastereoselectivity. The boryl group is a good latent functional group, and subsequent manipulations provide a variety of β-functionalized α-aminosilanes of great potential in medicinal chem. Addnl., preliminary application to asym. catalysis is also described. In the experiment, the researchers used (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: 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 aldehydesCOA of Formula: C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis