Day: October 20, 2022

In 2016,Ge, Chen; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia published 《Cu(I)-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with 2-Aryl-N-sulfonylaziridines as Alkylating Agents》.Organic Letters 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:

A highly enantioselective Friedel-Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu(CH3CN)4BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process. The experimental process involved 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: 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 In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Size is Important: Artificial Catalyst Mimics Behavior of Natural Enzymes》 was published in iScience in 2020. These research results belong to Chen, Jianzhong; Gridnev, Ilya D.. Computed Properties of C38H28O4P2 The article mentions the following:

Heavily substituted (R)-DTBM-SegPHOS is active in the asym. Pd(II)-catalyzed hydrogenation or C-O bond cleavage of α-pivaloyloxy-1-(2-furyl)ethanone, whereas (R)-SegPHOS fails to catalyze either of these transformations. An extensive network of C-H···H-C interactions provided by the heavily substituted Ph rings of (R)-DTBM-SegPHOS leads to increased stabilities of all intermediates and transition states in the corresponding catalytic cycles compared with the unsubstituted analogs. Moreover, formation of the encounter complex and its rearrangement into the reactive species proceeds in a fashion similar to that seen in natural enzymic reactions. Computations demonstrate that this feature is the origin of enantioselection in asym. hydrogenation, since the stable precursor is formed only when the catalyst is approached by one prochiral plane of the substrate. The experimental part of the paper was very detailed, including the reaction process of (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

Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleIn 2022 ,《Rh(I)-catalyzed asymmetric transfer hydrogenation of α-enamidophosphonates to α-aminophosphonates》 was published in Tetrahedron. The article was written by Feng, Yuting; Viereck, Peter; Li, Shi-Guang; Tsantrizos, Youla S.. The article contains the following contents:

An asym. Rh-catalyzed transfer hydrogenation was developed for the conversion of α-enamidophosphonates to α-aminophosphonates (α-APs) using isopropanol as the hydride donor. This methodol. is amenable to a broad substrate scope. A library of structurally diverse α-APs was synthesized in moderate to good yield and enantiomeric excess, having a methylene moiety at Cβ and aryl, heteroaryl or alkyl side chains. In the experiment, the researchers used (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: 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.Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Enantioselective synthesis of chiral acylsilanes by copper/HZNU-Phos-catalyzed asymmetric conjugate addition of diethyzinc to α,β-unsaturated acylsilanes》 was written by Lv, Ji-Yuan; Xu, Zheng; Zheng, Zhan-Jiang; Li, Li; Cui, Yu-Ming; Cao, Jian; Yang, Ke-Fang; Xu, Li-Wen. Application of 210169-54-3This research focused onunsaturated acylsilane preparation copper catalyzed asym conjugate addition diethyzinc; chiral acylsilane preparation. The article conveys some information:

The catalytic asym. Cu-catalyzed conjugate addition of diethylzinc to α,β-unsaturated acylsilanes proceeds smoothly in moderate to good yields and promising enantioselectivities (up to 85% ee) in the presence of the multifunctional HZNU-Phos with both a phosphine center and BINOL-based diol moiety that played a crucial role in the achievement of the best enantioselectivity for this reaction. In the experiment, the researchers used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Application 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.Application of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Deng, Hao; Dong, Yujie; Shangguan, Yu; Yang, Fazhou; Han, Sheng; Wu, Jiaqi; Liang, Bo; Guo, Hongchao; Zhang, Cheng published their research in Organic Letters in 2021. The article was titled 《Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles》.SDS of cas: 210169-54-3 The article contains the following contents:

A diastereoselective copper and NHC-ligand-catalyzed three-component difunctionalization of allenes RCH:C:CH2 with bis(pinacolato)diboron and 2H-azirines Ar1CHC(N)CAr2 to afford borylated allylaziridines Ar1CHC(NH)CAr2CHRC(Bpin):CH2 is described. The reaction exhibits complete diastereoselectivity and good yields, and the further chlorination of the corresponding borylated products was also performed. It is believed that the high ring-strain force of 2H-azirines facilitates the reaction. More chem. transformations of borylated allylaziridines are also reported.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3SDS of cas: 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.SDS of cas: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Liu, Gang; Yin, Congcong; Yang, Xuanliang; Li, Anqi; Wang, Minyan; Zhang, Xumu; Dong, Xiu-Qin published their research in Organic Letters in 2021. The article was titled 《Highly chemo- and enantioselective Rh-catalyzed hydrogenation of β-sulfonyl-α,β-unsaturated ketones: Access to chiral γ-ketosulfones》.Synthetic Route of C38H28O4P2 The article contains the following contents:

Rh-catalyzed highly chemo- and enantioselective hydrogenation of β-sulfonyl-α,β-unsaturated ketones was first successfully developed. Remarkably, a variety of enantioenriched γ-ketosulfones were generated in good to high yields with excellent chemo/enantioselectivities (82-99% yields, >99:1 chemoselectivity, 88 to >99% ee). Moreover, the gram-scale asym. hydrogenation was carried out smoothly in 97% yield and 97% ee. Preliminary DFT computations furnished a reasonable explanation for the high chemoselectivity and enantioselectivity. The experimental process involved 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) 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

Yuan, Wei; You, Lijun; Lin, Weidong; Ke, Jie; Li, Yingzi; He, Chuan published their research in Organic Letters in 2021. The article was titled 《Asymmetric Synthesis of Silicon-Stereogenic Monohydrosilanes by Dehydrogenative C-H Silylation》.Recommanded Product: (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article contains the following contents:

An asym. synthesis of silicon-stereogenic monohydrosilanes, e.g. I, by rhodium-catalyzed dehydrogenative C-H silylation is developed. The process is suitable for the synthesis of various asym. trisubstituted 1H-benzosiloles and 1H-benzosilolometallocenes in good yields with excellent chemo-, regio-, and stereocontrol. These selected silicon-stereogenic 1H-benzosilole compounds exhibit bright blue fluorescence and CPL (circular polarized luminescence) signals, which could be attractive to practitioners of materials science. 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) 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.Recommanded Product: (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Zhao, Zhi; Yang, Xing-Xing; Ran, Guang-Yao; Ouyang, Qin; Du, Wei; Chen, Ying-Chun published an article in 2021. The article was titled 《Ligand-Controlled Regiodivergent Asymmetric [5 + 2] and [3 + 2] Annulations of Vinyl Indoloxazolidones Catalyzed by Palladium》, and you may find the article in Organic Letters.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The information in the text is summarized as follows:

Here, authors present palladium-catalyzed regiodivergent asym. annulations of vinyl indoloxazolidones, which can act as 1,5-carbodipoles or 1,3-carbodipoles by tuning the chiral ligands and conditions, in the assemblies with sulfamate-derived cyclic imines and even activated alkenes. A diversity of polycyclic products are generally constructed with high regio- and enantioselectivity. 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: 210169-54-3Safety 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) 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.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones》 was published in Chemical Science in 2020. These research results belong to Cui, Jin; Kumagai, Naoya; Watanabe, Takumi; Shibasaki, Masakatsu. COA of Formula: C50H56O14P2 The article mentions the following:

An anti-selective catalytic asym. Michael-type vinylogous addition of β,γ-butenolides to chromones was developed. The catalyst system developed herein is characterized by tuning of the steric and electronic effects using a proper Biphep-type chiral ligand to invert the diastereoselection, and improvement of the catalyst turnover by a coordinative phenolic additive. The catalytic protocol renders potentially biol. active natural product analogs accessible in good yield with moderate diastereoselectivity and high enantiomeric purity, mostly greater than 99% ee. 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: 256390-47-3COA of Formula: 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. 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. COA of Formula: C50H56O14P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Computed Properties of C43H63FeNP2On March 10, 2016, Maj, Anna M.; Heyte, Svetlana; Araque, Marcia; Dumeignil, Franck; Paul, Sebastien; Suisse, Isabelle; Agbossou-Niedercorn, Francine published an article in Tetrahedron. The article was 《First catalytic asymmetric hydrogenation of quinoxaline-2-carboxylates》. The article mentions the following:

For the first time, the asym. hydrogenation of quinoxaline-2-carboxylates was performed successfully. The best catalysts are based on iridium complexes modified by chiral phosphorous ligands. Accelerated examination of ligands and catalysts has been undertaken by using a Chemspeed workstation (automated instrument) workstation enables carrying out, in parallel, eight independent catalytic reactions at the laboratory scale. Tetrahydroquinoxaline-2-carboxylates could be obtained with high yields and up to 74% ee. The synthesis of the target compounds was achieved using chiral ligands, such as (11aR)-10,11,12,13-tetrahydro-N,N-dimethyldiindeno[7,1-de:1′,7′-fg][1,3,2]dioxaphosphocin-5-amine [i/e/. (R)-siphos], 1,1′-[(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[1,1-diphenylphosphine] [i.e., (S)-MeO-BIPHEP], (R)-Cl-MeO-BIPHEP, (R)-difluorphos, (R)-GARPHOS, (R)-P-PHOS, (S)-C3-TUNEPHOS [i.e., 1,1′-[(13aS)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-diyl]bis[1,1-diphenylphosphine]], (S)-SEGPHOS, (S)-Xyl-SolPhos, CATASium T3, N-[(1R)-2-[(11bR)-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yloxy]-1-methylethyl]-N’-phenylurea [i.e., ureaphos], SL-J404-1, SL-J006-1, SL-J002-1, SL-J003-1, SL-J009-1, SL-T002-1, SL-W006-1. Pre-catalysts included bis(acetato-κO,κO’)[(4R)-1,1′-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]]ruthenium [i.e., Ru(OAc)2[(R)-segphos]], [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium [i.e., RuCl[(R,R)-TsDPEN][p-cymene]] and [1,1′-(1S)-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]][4-cyano-3-nitrobenzenecarboxylato(2-)-κC6,κO1](η3-2-propen-1-yl)iridium. In the experimental materials used by the author, we found (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Computed Properties of C43H63FeNP2)

(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3) 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. Computed Properties of C43H63FeNP2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis