Day: October 14, 2022

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

Porwanski, Stanislaw published an article in Carbohydrate Research. The title of the article was 《New ureas containing glycosyl and diphenylphosphinyl scaffolds: synthesis and the first attempts to use them in asymmetric synthesis》.Computed Properties of C22H22NP The author mentioned the following in the article:

Chiral ureas containing glycosyl and diphenylphosphinyl scaffolds, e.g. I, were found to be an effective organocatalyst. They were synthesized in high yields by a one-pot tandem Staudinger/aza-Wittig coupling reaction. The first attempts of using them in asym. synthesis are presented. Yields of the Morita-Baylis-Hillman reaction were moderate with an enantiomeric excess of up to 80%. In the part of experimental materials, we found many familiar compounds, such as (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas: 960128-64-7Computed Properties of C22H22NP)

(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.Computed Properties of C22H22NP 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 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

《Copper-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Dienes》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to He, Cheng-Yu; Li, Qing-Hua; Wang, Xin; Wang, Feng; Tian, Ping; Lin, Guo-Qiang. Product Details of 256390-47-3 The article mentions the following:

Due to the low reactivity of 1,6-dienes and the challenge of selectively differentiating such two olefins, the development of metal-catalyzed asym. cyclization of 1,6-dienes remains largely underdeveloped. Herein, the authors describe the 1st Cu(I)-catalyzed asym. borylative cyclization of cyclohexadienone-tethered terminal alkenes (1,6-dienes) via a tandem process: the regioselective borocupration of the electron-rich terminal alkene and subsequent conjugate addition of stereospecific secondary alkyl-Cu(I) to the electron-deficient cyclohexadienone, affording enantioenriched bicyclic skeletons bearing three contiguous stereocenters in all cis-form. Meanwhile, this mild catalytic protocol is generally compatible with a wide range of functional groups, which allows further facile conversion of the cyclization products.(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Product Details of 256390-47-3) was used in this study.

(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. Product Details of 256390-47-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2017,Chemistry – A European Journal included an article by Zhang, Wanli; Ma, Shengming. Recommanded Product: 256390-47-3. The article was titled 《Palladium-Catalyzed Enantioselective Alkoxycarbonylation of Propargylic Carbonates with (R)- or (S)-3,4,5-(MeO)3-MeOBIPHEP》. The information in the text is summarized as follows:

(R)- and (S)-3,4,5-(MeO)3-MeOBIPHEP were identified as the efficient chiral ligands for the Pd-catalyzed highly enantioselective synthesis of 2,3-allenoates from different types of easily available racemic propargylic carbonates with 90-98% ee and decent yields. The potential of the products was demonstrated with high chirality transfer efficiency. In addition to this study using (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine], there are many other studies that have used (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Recommanded Product: 256390-47-3) was used in this study.

(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. Recommanded Product: 256390-47-3

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

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

Electric Literature of C50H56O14P2On June 5, 2015, Murai, Masahito; Takeshima, Hirotaka; Morita, Haruka; Kuninobu, Yoichiro; Takai, Kazuhiko published an article in Journal of Organic Chemistry. The article was 《Acceleration effects of phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds》. The article mentions the following:

The current work describes the marked rate of acceleration caused by phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds. The reactivity was affected by the steric and electronic nature of the phosphine ligands. The use of the bulky and electron-rich diphosphine ligand (R)-DTBM-SEGPHOS was highly effective to yield the dehydrogenative silylation products selectively in the presence of a hydrogen acceptor. An appropriate choice of C2-sym. chiral diphosphine ligand enables the asym. dehydrogenative silylation via the enantioselective desymmetrization of the C(sp3)-H bond. The unprecedented catalytic germylation of C(sp3)-H bonds with dehydrogenation was also examined with the combination of the rhodium complex and a wide bite angle diphosphine ligand to provide the corresponding 2,3-dihydrobenzo[b]germoles in good yield. 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: 256390-47-3Electric Literature of 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. Electric Literature of 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

In 2019,Organic & Biomolecular Chemistry included an article by Wang, Kaiye; Xiang, Yanan; Shi, Zhujun; Wang, Hongyu; Li, Na; Tang, Bo. Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine. The article was titled 《Asymmetric kinetic resolution of sulfides for the construction of unsymmetric sulfides and chiral 3,3-disubstituted oxindoles》. The information in the text is summarized as follows:

An enantioselective method was developed for the synthesis of unsym. disulfides R’SSR” [R’ = allyl, CH2CO2Me, Bn, etc.; R” = 4-FC6H4, 4-BrC6H4, Bn] and chiral 3,3-disubstituted oxindoles I [R1 = allyl, 4-BrC6H4, Bn, etc.; X = H, 5-Br, 5-I, 6-Br; R2 = Me, PMB] in one step from oxindoles and thiols using chiral phosphines catalyst. Many substituted thiols and 3,3-disubstituted oxindoles were well tolerated and produced high yields and enantioselectivities under mild conditions. In the experimental materials used by the author, we found (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