Category: 210169-54-3

In 2022,Chen, Wenchang; Yi, Xiaofen; Qu, Hongmin; Chen, Yu; Tang, Pei; Chen, Fener published an article in Chinese Chemical Letters. The title of the article was 《Concise syntheses of 13-methylprotoberberine and 13-methyltetrahydroprotoberberine alkaloids》.Product Details of 210169-54-3 The author mentioned the following in the article:

The concise syntheses of eight 13-methylprotoberberine (13-MePB) and eight enantioenriched 13-methyltetrahydroprotoberberine (13-MeTHPB) alkaloids have been achieved in a tactically modular fashion. This synthetic work features a one-pot metal-free Pictet-Spengler/Friedel-Crafts hydroxyalkylation/dehydration/oxidation sequence and a following highly enantioselective Ir-catalyzed hydrogenation. Given such brevity and modularity, our developed synthetic route would be greatly beneficial to the efficient syntheses of existing natural products and new fully synthetic variants of 13-MePB and 13-MeTHPB family. 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: 210169-54-3Product Details of 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 aldehydesProduct Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Mechanistic insights into Cu-catalyzed enantioselective Friedel-Crafts reaction between indoles and 2-aryl-N-sulfonylaziridines》 was written by Wang, Ping; Zhao, Yang; Chapagain, Biplav; Yang, Yonggang; Liu, Wei; Wang, Yong. Product Details of 210169-54-3 And the article was included in Catalysis Science & Technology in 2020. The article conveys some information:

Computational studies were successfully carried out to provide mechanistic insights into LCu-catalyzed (L = (S)-Segphos ligand) Friedel-Crafts (F-C) reaction between indoles and 2-aryl-N-sulfonylaziridines. The proposed enantioselective mechanistic roles for the LCu-catalyzed F-C reaction were carefully considered: C-N bond cleavage through a three-membered ring transition state, C-C bond formation, oxidative addition, and reductive elimination. Through the energy decomposition anal. (EDA) on all possible transition states of the rate-determining step (RDS), the smaller ΔEdef(total) and the larger ΔEint were found in TS3R, resulting in the lowest activation energy (ΔE#). In other words, TS3R was the most kinetically favorable with the lowest activation barrier. Afterwards, the noncovalent interactions (C-H···π and π···π) and the steric effects were identified as playing a pivotal role in a favorable transition state for the C-C bond formation. In addition, the frontier MO (FMO) revealed that the smallest energy gap (5.2836 eV) between the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) was found in TS3R.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Product Details of 210169-54-3) 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.Product Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleIn 2016 ,《Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines》 appeared in Chemistry – A European Journal. The author of the article were Yan, Liang; Xu, Jing-Kun; Huang, Chao-Fan; He, Zeng-Yang; Xu, Ya-Nan; Tian, Shi-Kai. The article conveys some information:

A new strategy has been established for the kinetic resolution of racemic allylic alcs. through a palladium/sulfonyl-hydrazide-catalyzed asym. OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2, 4 mol % (S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcs. were smoothly resolved with selectivity factors of more than 400 through an asym. allylic alkylation of monosubstituted hydrazines under air at room temperature Importantly, this kinetic resolution process provided various allylic alcs. and allylic hydrazine derivatives with high enantiopurity. The results came from multiple reactions, including 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) 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 aldehydesSafety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Xiao, Xiong; Yu, Zhi-Xiang published their research in Chemistry – A European Journal in 2021. The article was titled 《Co-Catalyzed Asymmetric Intramolecular [3+2] Cycloaddition of Yne-Alkylidenecyclopropanes and its Reaction Mechanism》.Application In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article contains the following contents:

Developing new transition metal-catalyzed asym. cycloadditions for the synthesis of five-membered carbocycles (FMCs) is a research frontier in reaction development due to the ubiquitous presence of chiral FMCs in various functional mols. Reported here is our discovery of a highly enantioselective intramol. [3+2] cycloaddition of yne-alkylidenecyclopropanes (yne-ACPs) to bicyclo[3.3.0]octadiene, e.g., I, and bicyclo[4.3.0]nonadiene mols. using a cheap Co catalyst and com. available chiral ligand (S)-Xyl-BINAP. This reaction avoids the use of precious Pd and Rh catalysts, which are usually the choices for [3+2] reactions with ACPs. The enantiomeric excess in the present reaction can be up to 92%. Cationic cobalt(I) species was suggested by experiments as the catalytic species. DFT calculations showed that this [3+2] reaction starts with oxidative cyclometallation of alkyne and ACP, followed by ring opening of the cyclopropyl (CP) group and reductive elimination to form the cycloadduct. This mechanism is different from previous [3+2] reactions of ACPs, which usually start from CP cleavage, not from oxidative cyclization. The results came from multiple reactions, including the reaction of (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

In 2022,Li, Guanlin; Zhao, Ling; Luo, Yicong; Peng, Youbin; Xu, Kai; Huo, Xiaohong; Zhang, Wanbin published an article in Chemistry – A European Journal. The title of the article was 《Stereodivergent Desymmetrization of Simple Dicarboxylates via Branch-Selective Pd/Cu Catalyzed Allylic Substitution》.Category: chiral-phosphine-ligands The author mentioned the following in the article:

Asym. desymmetrization has been demonstrated to be a powerful strategy for building stereocenters in asym. synthesis. Herein, a Pd/Cu catalyzed asym. desymmetrization reaction with a simple geminal dicarboxylate is reported. A wide scope of imino esters bearing an aryl or heteroaromatic group were compatible with this bimetallic catalytic system. The reactions proceeded smoothly, giving the desired products in good yields with high to excellent regio-, diastereo-, and enantioselectivity (up to 20 : 1 branched:linear, >20 : 1 dr, >99% ee). Notably, the reaction favored branched selectivity, which is unusual for the Pd-catalyzed allylic alkylation reaction. In addition, the standard product could be easily transformed to other valuable mols. such as chiral allylic alcs., carbamates, and organic boron compounds Furthermore, DFT calculations were conducted to explain the origin of the branched selectivity. The results came from multiple reactions, including the reaction of (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

In 2017,Jiao, Yunzhe; Torne, Marta Serrano; Gracia, Jose; Niemantsverdriet, J. W.; van Leeuwen, Piet W. N. M. published 《Ligand effects in rhodium-catalyzed hydroformylation with bisphosphines: steric or electronic?》.Catalysis Science & Technology published the findings.Product Details of 210169-54-3 The information in the text is summarized as follows:

Twelve com. available bisphosphine ligands were evaluated in rhodium-catalyzed hydroformylation reactions. All ligands exhibited high chemoselectivities for aldehyde formation. The highest enantioselectivity (53% ee) of styrene hydroformylation was achieved with (S)-BTFM-Garphos (L7) substituted with electron withdrawing substituents. High pressure NMR (HP-NMR) spectroscopy and in situ high pressure IR spectroscopy (HP-IR) were used to study the resting states of the catalyst species in the reactions. The ligand effect on the structures of the observable species was examined Both electronic and steric factors were considered to contribute to the performance of the various ligands. Decreasing the phosphine basicity increased the enantioselectivity, while in the systems studied here the steric character plays a less important role than the electronic features in achieving good regioselectivities. After reading the article, we found that the author used (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) 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 aldehydesProduct Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2017,Xia, Yun-Tao; Ma, Jing; Wang, Xiao-Dong; Yang, Lei; Wu, Lei published 《Enantioselective hydrogenation of N-heteroaromatics catalyzed by chiral diphosphine modified binaphthyl palladium nanoparticles》.Catalysis Science & Technology published the findings.SDS of cas: 210169-54-3 The information in the text is summarized as follows:

The first application of binaphthyl-stabilized palladium nanoparticles (Bin-PdNPs) with chiral modifiers in asym. hydrogenation of N-heteroaromatics was revealed. With an appropriate ratio of R-BINAP/Bin-PdNPs used, the pre-prepared chiral nanocatalyst achieved asym. hydrogenations of 2-substituted quinolines with good to excellent yields and moderate enantioselectivities, which showed superior catalytic properties to the R-BINAP/Pd complex. Moreover, this protocol was also applicable to 2-substituted indoles. The experimental process involved the reaction 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

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

Recommanded Product: (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleIn 2016 ,《Enantioselective Rhodium-Catalyzed Dearomative Arylation or Alkenylation of Quinolinium Salts》 was published in Angewandte Chemie, International Edition. The article was written by Wang, Yan; Liu, Yunlong; Zhang, Dongdong; Wei, Hao; Shi, Min; Wang, Feijun. The article contains the following contents:

A highly enantioselective rhodium(I)-catalyzed dearomative arylation or alkenylation of easily available N-alkylquinolinium salts is reported, thus providing an effective and practical approach to the synthesis of dihydroquinolines in up to 99% ee. This reaction tolerates a wide range of functional groups with respect to both the organic boronic acids and the quinoline starting materials. Moreover, the synthetic utility of this protocol is demonstrated in the formal asym. synthesis of bioactive tetrahydroquinoline and the total syntheses of (-)-angustureine and (+)-cuspareine. 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: (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

Recommanded Product: 210169-54-3In 2018 ,《Palladium-Catalyzed Enantioselective Intramolecular Dearomative Heck Reaction》 was published in Journal of the American Chemical Society. The article was written by Li, Xiang; Zhou, Bo; Yang, Run-Ze; Yang, Fu-Ming; Liang, Ren-Xiao; Liu, Ren-Rong; Jia, Yi-Xia. The article contains the following contents:

Enantioselective intramol. dearomative Heck reactions have been developed by Pd-catalyzed cross-coupling of aryl halides or aryl triflates with the internal C=C bond of indoles, benzofurans, pyrroles, and furans. A variety of structurally unique spiroheterocycles and benzofused heterocycles having N/O-substituted quaternary carbon stereocenters, and exocyclic olefin moieties were afforded in moderate to excellent yields with good to excellent enantioselectivities, showing a broad scope of the present protocol. A series of new BINOL- and H8-BINOL-based phosphoramidite ligands were synthesized and proved to be efficient chiral ligands in the reactions of C2-tethered substrates to form spiroheterocycles. (S)-SEGPHOS turned out to be a good ligand for the reaction delivering benzofused indolines and pyrrolines. Synthetic applications based on transformations of the exocyclic double bonds were realized without loss of enantiopurities, including hydrogenation, hydroborylation, and stereospecific ring-expanding rearrangement. In addition to this study using (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, there are many other studies that have used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Recommanded Product: 210169-54-3) was used in this study.

(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