Tag: 600-700

In 2018,Lou, Yazhou; Hu, Yutao; Lu, Jiaxiang; Guan, Fanfu; Gong, Gelin; Yin, Qin; Zhang, Xumu published 《Dynamic Kinetic Asymmetric Reductive Amination: Synthesis of Chiral Primary β-Amino Lactams》.Angewandte Chemie, International Edition published the findings.Computed Properties of C38H28O4P2 The information in the text is summarized as follows:

A highly efficient ruthenium-catalyzed asym. reductive amination (ARA) of racemic β-keto lactams with mol. hydrogen and ammonium salts is disclosed for the synthesis of enantiomerically pure primary amino lactams through dynamic kinetic resolution (DKR). By this approach, a range of syn primary β-amino lactams I (R= Me, Et, iso-Pr etc. n= 1, 2) were obtained in high yields with high chemo-, enantio-, and diastereoselectivity (up to 98 % yield, 99 % ee, >20:1 d.r., syn products). The utility of the products has been demonstrated by rapid access to a key synthetic intermediate towards biol. active drug mols. Meanwhile, mechanistic studies and control experiments indicate that the reaction may proceed through the hydrogenation of an iminium intermediate. In the experiment, the researchers used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Computed Properties 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.Computed Properties of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleIn 2017 ,《Rhodium-catalyzed hydroformylation in γ-valerolactone as a biomass-derived solvent》 was published in Journal of Organometallic Chemistry. The article was written by Pongracz, Peter; Bartal, Brigitta; Kollar, Laszlo; Mika, Laszlo T.. The article contains the following contents:

Rhodium-catalyzed hydroformylation of styrene, α-methylstyrene, di-Me itaconate, and (R)-limonene was performed in gamma-valerolactone (GVL) as a proposed biomass-based environmentally benign solvent for hydroformylation referring to toluene as a generally used conventional solvent. Both achiral (triphenylphosphine, 1,3-bis(diphenylphoshino)propane) and enantiopure bidentate phosphine ligands ((S,S)-BDPP, (R)-BINAP, (R)-QUINAP, (R,R)-DIOP, (Rc),(Sp)-JOSIPHOS, (S)-SEGPHOS, (S)-(DM)-SEGPHOS) were investigated in in situ generated Rh-diphosphine catalyst systems. In general, the catalysts’ activity in GVL was lower than in toluene; however, remarkable chemo- (>99%) and regioselectivities (>95%) were achieved in GVL under identical conditions. The BDPP-modified Rh-catalyst was recycled for three consecutive cycles; however a decrease in its activity was detected. In the experiment, the researchers used many compounds, for example, (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Quality Control 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.Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2018,Gupta, Naveen; Tak, Rajkumar; Nazish, Mohd; Jakhar, Ajay; Khan, Noor-ul H.; Kureshy, Rukhsana I. published 《Copper(II) Triflate Catalyzed Regioselective and Enantioselective Propargylation of Isatin Derivatives by Using Allenylboronic Acid Pinacol Ester》.European Journal of Organic Chemistry published the findings.COA of Formula: C38H28O4P2 The information in the text is summarized as follows:

The authors report a simple protocol for the synthesis of homopropargyl alcs. with isatin derivatives under milder conditions for the first time. The excellent regioselectivity and yields were observed with copper triflate as a Lewis-acid catalyst and allenylboronic acid pinacol ester as a nucleophile in aqueous media. A gram-scale synthesis was done to check the efficiency of the protocol with retention in selectivity. Further one-step functionalization of these homopropargyl alcs. was established as the synthetic application of these alkynes. The enantioselective synthesis of these chiral propargyl alcs. also was explored for the first time with an enantiomeric ratio up to 12:88. In the experiment, the researchers used many compounds, for example, (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

In 2017,Zhou, Huan; Liu, Yuan; Yang, Suhua; Zhou, Le; Chang, Mingxin published 《One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines》.Angewandte Chemie, International Edition published the findings.Application of 210169-54-3 The information in the text is summarized as follows:

A one-pot N-Boc deprotection and catalytic intramol. reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: titanium(IV) isopropoxide and mol. iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Application 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: 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 aldehydesApplication of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Zhang, Jiacheng; Huo, Xiaohong; Xiao, Junzhe; Zhao, Ling; Ma, Shengming; Zhang, Wanbin published their research in Journal of the American Chemical Society in 2021. The article was titled 《Enantio- and Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu Catalysis》.Computed Properties of C38H28O4P2 The article contains the following contents:

Herein, an enantio- and diastereodivergent construction of 1,3-nonadjacent stereocenters bearing allenyl axial and central chirality through synergistic Pd/Cu-catalyzed dynamic kinetic asym. allenylation with racemic allenylic esters was reported. The protocol was suitable for a wide range of substrates including the challenging allenylic esters with less sterically bulky substituents and provided chiral allenylic products I [R = n-Bu, Ph, CMe2OTBS, etc.; Ar = Ph, 2-naphthyl, 2-furyl, etc.; stereo = R or S] bearing 1,3-nonadjacent stereocenters with high levels of enantio- and diastereoselectivities (up to >20:1 dr and >99% ee). Furthermore, several representative transformations involving axial-to-central chirality transfer were conducted, affording useful structural motifs containing nonadjacent stereocenters in a diastereodivergent manner. In the experiment, the researchers used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Computed Properties 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.Computed Properties of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2018,Trost, Barry M.; Bai, Wen-Ju; Stivala, Craig E.; Hohn, Christoph; Poock, Caroline; Heinrich, Marc; Xu, Shiyan; Rey, Jullien published 《Enantioselective Synthesis of des-Epoxy-Amphidinolide N》.Journal of the American Chemical Society published the findings.Synthetic Route of C38H28O4P2 The information in the text is summarized as follows:

The synthesis of des-epoxy-amphidinolide N (I) was achieved in 22 longest linear and 33 total steps. Three generations of synthetic endeavors are reported herein. During the first generation, our key stitching strategy that highlighted an intramol. Ru-catalyzed alkene-alkyne (Ru AA) coupling and a late-stage epoxidation proved successful, but the installation of the α,α’-dihydroxyl ketone motif employing a dihydroxylation method was problematic. Our second generation of synthetic efforts addressed the scalability problem of the southern fragment synthesis and significantly improved the efficiency of the atom-economical Ru AA coupling, but suffered from several protecting group-based issues that proved insurmountable. Finally, relying on a judicious protecting group strategy together with concise fragment preparation, des-epoxy-amphidinolide N was achieved in a convergent fashion. Calculations disclose a hydrogen-bonding bridge within amphidinolide N. Comparisons of 13C NMR chem. shift differences using our synthetic des-epoxy-amphidinolide N suggest that amphidinolide N and carbenolide I are probably identical. 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: 210169-54-3Synthetic Route of C38H28O4P2) 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.Synthetic Route of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Tandem Catalytic Indolization/Enantioconvergent Substitution of Alcohols by Borrowing Hydrogen to Access Tricyclic Indoles》 was written by Yang, Guoqiang; Pan, Jiaoting; Ke, Ya-Ming; Liu, Yongbing; Zhao, Yu. Name: (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleThis research focused ontricyclic indole preparation enantioselective; alc alkynyl aniline tandem indolization iridium phosphoric acid catalyst; enantioselectivity; hydrogen; redox-neutral catalysis; relay catalysis; tricyclic indoles. The article conveys some information:

An efficient tandem catalysis method is achieved for the direct conversion of alc.-containing alkynyl anilines 2-H2N-5-RC6H3CC(CH2)3CH(R1)OH (R = H, Me, t-Bu, F; R1 = Bu, cyclohexylmethyl, Ph, 2-naphthyl, furan-2-yl, etc.) to valuable chiral 2,3-fused tricyclic indoles (S)-I. This method relies on a tandem indolization followed by enantioconvergent substitution of alcs. via borrowing hydrogen to construct two rings in one step, enabled by relay and cooperative catalysis of a chiral iridium complex with a chiral phosphoric acid. Highly diastereoselective transformations of the tricyclic indole products (S)-I (R = H; R1 = isobutyl) also provide efficient access to a diverse array of complex polycyclic indoline compounds, e.g., II. In the experiment, the researchers used many compounds, for example, (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Name: (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.Name: (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Synthetic Route of C38H28O4P2In 2016 ,《Rhodium-Catalyzed Hydrocarboxylation of Olefins with Carbon Dioxide》 appeared in European Journal of Organic Chemistry. The author of the article were Kawashima, Shingo; Aikawa, Kohsuke; Mikami, Koichi. The article conveys some information:

The catalytic hydrocarboxylation of styrenes derivatives and α,β-unsaturated carbonyl compounds with CO2 (101.3 kPa) in the presence of an air-stable rhodium catalyst was explored. The combination of [RhCl(cod)]2 (cod = cyclooctadiene) as a catalyst and diethylzinc as a hydride source allowed for effective hydrocarboxylation and provided the corresponding α-aryl carboxylic acids in moderate to excellent yields. In this catalytic process with carbon dioxide, intervention of the RhI-H species, which could be generated from the RhI catalyst and diethylzinc, was clarified. Significantly, the catalytic asym. hydrocarboxylation of α,β-unsaturated esters with carbon dioxide was also performed by employing a cationic rhodium complex possessing (S)-(-)-4,4′-bi-1,3-benzodioxole-5,5′-diylbis(diphenylphosphine) [(S)-SEGPHOS] as a chiral diphosphine ligand. A plausible model for asym. induction was proposed by determination of the absolute configuration of the product.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Synthetic Route of C38H28O4P2) 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.Synthetic Route of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

HPLC of Formula: 210169-54-3In 2016 ,《Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium-Catalyzed [2+2+2] Cycloaddition》 appeared in Angewandte Chemie, International Edition. The author of the article were Masutomi, Koji; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken. The article conveys some information:

Cationic rhodium(I)/axially chiral biaryl bis(phosphine) complexes catalyze the asym. [2+2+2] cycloaddition of 1,6-enynes with electron-rich functionalized alkenes, enamides, and vinyl carboxylates, to produce the corresponding protected cyclohexenylamines and cyclohexenols. Regioselectivity depends on structures of substrates. The present cycloaddition was successfully applied to the enantioselective total synthesis of (-)-porosadienone by using the amide moiety as a leaving group. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3HPLC of Formula: 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.HPLC of Formula: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2019,Journal of the American Chemical Society included an article by Hong, Feng-Lin; Wang, Ze-Shu; Wei, Dong-Dong; Zhai, Tong-Yi; Deng, Guo-Cheng; Lu, Xin; Liu, Rai-Shung; Ye, Long-Wu. Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole. The article was titled 《Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles》. The information in the text is summarized as follows:

In the presence of Cu(MeCN)4PF6, N-propargyl vinylaryl ynamides such as I (Ts = 4-MeC6H4SO2) underwent diastereoselective cascade cyclization reactions via copper carbenes to yield cyclopropabenzoisoindoles such as II; when a nonracemic bisoxazoline ligand was used, the cyclopropabenzoisoindoles were prepared in 90:10-97:3 er. N-Propargyl aryl ynamides such as III underwent enantioselective cyclization reactions in the presence of Cu(MeCN)4PF6 and (R)- or (S)-Segphos to yield nonracemic indanopyrroles such as IV. Mechanistic studies revealed that donor/donor copper carbenes are involved in the 1,5-diyne cyclization reactions, in contrast to reactions of gold catalysts, and provides a novel method to generate donor/donor carbenes. 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) 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