Day: October 13, 2022

The author of 《Regioconvergent and Enantioselective Rhodium-Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles》 were Haydl, Alexander M.; Hilpert, Lukas J.; Breit, Bernhard. And the article was published in Chemistry – A European Journal in 2016. Quality Control of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene The author mentioned the following in the article:

In the presence of (cyclooctadiene)rhodium(I) chloride dimer, a nonracemic ferrocenyldiphosphine monoxide, and pyridine p-toluenesulfonate (PPTS), 1-aryl-1-propynes such as RCCMe (R = Ph, 4-MeC6H4, 4-F3CC6H4, 4-PhC6H4, 2-naphthyl, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeCOC6H4, 4-O2NC6H4, PinB; PinB = 4,4,5,5-tetramethyl-1,3-dioxo-2-borolan-2-yl), phenylallene, and selected 1-aryl-2-propynes underwent chemoselective, regioselective, and enantioselective addition reactions with 1H-pyrazoles to yield nonracemic N1-allylic pyrazoles such as I (R = Ph, 4-MeC6H4, 4-F3CC6H4, 4-PhC6H4, 2-naphthyl, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-MeCOC6H4, 4-O2NC6H4, PinB) in 65-97% yields, in 68:32->99:1 regioselectivities, and in 80:20-97.5:2.5 er (or, for nonracemic pyrazoles, 82:18 or 85:15 dr). The method tolerated a variety of functional groups in the alkyne and pyrazole components. The structure of a phenylallylated stanozolol was determined by X-ray crystallog. In the experimental materials used by the author, we found (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene(cas: 1221746-56-0Quality Control of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene)

(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene(cas: 1221746-56-0) 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. Quality Control of (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[(R)-phenylphosphinoyl]ferrocene

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

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

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

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

In 2009,Chemistry – A European Journal included an article by Hashmi, A. Stephen K.; Hamzic, Melissa; Rominger, Frank; Bats, Jan W.. Electric Literature of C50H56O14P2. The article was titled 《Gold Catalysis: Enantiotopos Selection》. The information in the text is summarized as follows:

The Au-catalyzed enantioselective cycloisomerization of furyldialkynes, e.g. I, for the preparation of phenols, e.g. II, was reported. 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

The author of 《Palladium-Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit》 were Li, Qiankun; Fu, Chunling; Ma, Shengming. And the article was published in Angewandte Chemie, International Edition in 2014. Formula: C50H56O14P2 The author mentioned the following in the article:

In the presence of a nonracemic bis[bis(trimethoxyphenyl)phosphino]biphenyl and bis(allylpalladium chloride) and using DBU in o-xylene, tosylamides RNHTs (R = H2C:CHCH2, Me2C:CHCH2, H2C:CMeCH2, HCCCH2, n-PrCCCH2, H2C:C:CHCH2, PhCH2, Me; Ts = 4-MeC6H4SO2) underwent regioselective and enantioselective substitution reactions with allenylmethyl phosphates H2C:C:CHCHR1OP(:O)(OEt)2 [R1 = BuCH2CH2, Bu, PhCH2CH2, H2C:CH(CH2)8, Cl(CH2)5, THPO(CH2)5, Me3SiCC(CH2)3, n-Pr; THP = tetrahydropyran-2-yl] to give nonracemic allenylmethylamines such as (S)-H2C:C:CHCHR1NRTs [R = H2C:CHCH2, Me2C:CHCH2, H2C:CMeCH2, HCCCH2, n-PrCCCH2, H2C:C:CHCH2, PhCH2, Me; R1 = BuCH2CH2, Bu, PhCH2CH2, H2C:CH(CH2)8, Cl(CH2)5, HO(CH2)5, Me3SiCC(CH2)3, n-Pr] (I) in 47-90% yields and in 88-94% ee. The structure of a nonracemic cyclopentapyridinone dinitrophenylhydrazone derived from I (R = n-PrCCCH2; R1 = BuCH2CH2) in two steps was determined by X-ray crystallog. 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: 256390-47-3Formula: C50H56O14P2) 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. Formula: C50H56O14P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2016,Kita, Yusuke; Hida, Shoji; Higashihara, Kenya; Jena, Himanshu Sekhar; Higashida, Kosuke; Mashima, Kazushi published 《Chloride-Bridged Dinuclear Rhodium(III) Complexes Bearing Chiral Diphosphine Ligands: Catalyst Precursors for Asymmetric Hydrogenation of Simple Olefins》.Angewandte Chemie, International Edition published the findings.Electric Literature of C38H28O4P2 The information in the text is summarized as follows:

Efficient rhodium(III) catalysts were developed for asym. hydrogenation of simple olefins. A series of chloride-bridged dinuclear rhodium(III) complexes were synthesized from the rhodium(I) precursor [RhCl(cod)]2, chiral diphosphine ligands, and hydrochloric acid. Complexes from the series acted as efficient catalysts for asym. hydrogenation of (E)-prop-1-ene-1,2-diyldibenzene and its derivatives without any directing groups, in sharp contrast to widely used rhodium(I) catalytic systems that require a directing group for high enantioselectivity. The catalytic system was applied to asym. hydrogenation of allylic alcs., alkenylboranes, and unsaturated cyclic sulfones. Control experiments support the superiority of dinuclear rhodium(III) complexes over typical rhodium(I) catalytic systems. 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: 210169-54-3Electric Literature 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.Electric Literature of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Zhang, Jinyu; Yan, Nuo; Ju, Cheng-Wei; Zhao, Dongbing published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Nickel(0)-Catalyzed Asymmetric Ring Expansion Toward Enantioenriched Silicon-Stereogenic Benzosiloles》.Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article contains the following contents:

The development of a straightforward strategy to obtain enantioenriched silicon-stereogenic benzosiloles remains a challenging yet appealing synthesis venture due to their potential future application in chiral electronic and optoelectronic devices. In this context, all of the existing methods rely on Rh-catalyzed systems and are somewhat limited in scope. Herein, we disclose the first Ni0-catalyzed ring expansion process that enables the preparation of benzosiloles possessing tetraorganosilicon stereocenters in excellent yields and enantioselectivities. The presented catalysis strategy is further applied to the asym. synthesis of silicon-stereogenic bis-silicon-bridged π-extended systems. Preliminary studies reveal that such compounds exhibit fluorescence emission, Cotton effects and circularly polarized luminescence (CPL) activity. After reading the article, we found that the author 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

Recommanded Product: 210169-54-3In 2016 ,《Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines》 appeared in Journal of the American Chemical Society. The author of the article were Kubota, Koji; Watanabe, Yuta; Hayama, Keiichi; Ito, Hajime. The article conveys some information:

We have developed a novel approach for the synthesis of enantioenriched 3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-, and enantioselective protoborylation of 1,2-dihydropyridines, which were obtained by the partial reduction of the pyridine derivatives This dearomatization/enantioselective borylation stepwise strategy provides facile access to chiral piperidines together with the stereospecific transformation of a stereogenic C-B bond from readily available starting materials. Furthermore, the utility of this method is demonstrated for the concise synthesis of the antidepressant drug (-)-paroxetine. A theor. study of the reaction mechanism is also described. After reading the article, we found that the author used (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) 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: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Product Details of 210169-54-3In 2022 ,《Catalytic Regio- and Enantioselective Protonation for the Synthesis of Chiral Allenes: Synergistic Effect of the Counterion and Water》 was published in Angewandte Chemie, International Edition. The article was written by Lin, Qianchi; Zheng, Sujuan; Chen, Long; Wu, Jin; Li, Jinzhao; Liu, Peizhi; Dong, Shunxi; Liu, Xiaohua; Peng, Qian; Feng, Xiaoming. The article contains the following contents:

A highly enantioselective tandem Pudovik addition/[1,2]-phospha-Brook rearrangement of α-alkynylketoamides with diarylphosphine oxides was achieved with a N,N’-dioxide/ScIII complex as the catalyst. This protocol features broad substrate scope, high regio- and enantioselectivity, and good functional-group compatibility, providing a straightforward route to various trisubstituted allenes with a diarylphosphinate functionality in good yields with high enantioselectivities (up to 97% yield, 96% ee). Control experiments and theor. calculations revealed that a synergistic effect of the counterion and water was critical for the regio- and enantioselective protonation after [1,2]-phospha-Brook rearrangement. The synthetic utility of this methodol. was demonstrated by the conversion of products into complex bridged polycyclic architectures through intramol. dearomatizing arene/allene cycloaddition 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: 210169-54-3Product 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