Category: chiral-phosphine-ligands

An Enantioselective Total Synthesis of (-)-Isoschizogamine was written by Xu, Zhengren;Bao, Xu;Wang, Qian;Zhu, Jieping. And the article was included in Angewandte Chemie, International Edition in 2015.Product Details of 1006708-91-3 This article mentions the following:

A concise enantioselective total synthesis of (-)-isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N-Alkylation of an enantio-enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by microwave irradiation in the presence of pivalic acid, was converted into the hexacyclic structure of natural product by a complex but ordered domino sequence. The one-pot process leading to the formation of one C-C bond and three C-N bonds created three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochem. In the experiment, the researchers used many compounds, for example, (R)-2-(2-(Bis(4-(trifluoromethyl)phenyl)phosphino)-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole (cas: 1006708-91-3Product Details of 1006708-91-3).

(R)-2-(2-(Bis(4-(trifluoromethyl)phenyl)phosphino)-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole (cas: 1006708-91-3) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Product Details of 1006708-91-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

New chiral ferrocenyl P,S-ligands for highly diastereo-/enantioselective catalytic [3 + 2] cycloaddition of azomethine ylides with cyclic and acyclic enones was written by Zhang, Cheng;Yu, Sai-Bo;Hu, Xiang-Ping;Wang, Dao-Yong;Zheng, Zhuo. And the article was included in Organic Letters in 2010.Name: (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine This article mentions the following:

A new family of chiral ferrocenyl P,S-ligands I (R = Me, i-Pr, Ph, 4-ClC₆H₄, 4-MeC₆H₄, PhCH₂) has been developed and successfully applied in a highly endo-selective catalytic asym. cycloaddition of azomethine ylides with various enones, including cyclic and acyclic α-enones. For cyclic α-enones, [Cu(CH₃CN)₄]ClO₄/(R_c,S_Fc)-I (R = i-Pr) complex catalyzed the cycloaddition to give the sole endo-cycloadducts in perfect enantioselectivities (normally 99% ee), while AgOAc/(R_c,S_Fc)-I (R = i-Pr) catalytic system exhibited good endo/exo selectivities (endo/exo = 91/9 to 96/4) and high enantiocontrol (up to 98% ee) for acyclic α-enones. In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2Name: (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Name: (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Bifunctional ferrocene-based squaramide-phosphine as an organocatalyst for highly enantioselective intramolecular Morita-Baylis-Hillman reaction was written by Zhang, Xiaorui;Ma, Pengfei;Zhang, Dongxu;Lei, Yang;Zhang, Shengyong;Jiang, Ru;Chen, Weiping. And the article was included in Organic & Biomolecular Chemistry in 2014.Electric Literature of C26H28FeNP This article mentions the following:

This work demonstrates that, in accord with metal catalysis, ferrocene could be an excellent scaffold for organocatalysts. The simple and easily accessible bifunctional ferrocene-based squaramide-phosphine shows high enantioselectivity in the intramol. Morita-Baylis-Hillman reaction of 7-aryl-7-oxo-5-heptenals, giving a variety of 2-aroyl-2-cyclohexenols in up to 96% ee. In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2Electric Literature of C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Electric Literature of C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Copper(I) Alkoxide-Catalyzed Alkynylation of Trifluoromethyl Ketones was written by Motoki, Rie;Kanai, Motomu;Shibasaki, Masakatsu. And the article was included in Organic Letters in 2007.Related Products of 352655-61-9 This article mentions the following:

A general method for direct alkynylation of trifluoromethyl ketones to afford the corresponding tertiary propargyl alcs., e.g., I, was developed using CuO^tBu-xantphos or phenanthroline complexes as catalysts. The ligands significantly enhanced the catalyst activity. In addition, KOTf, generated in the catalyst preparation step, exhibited some acceleration effects. A preliminary extension to a catalytic enantioselective CF₃-substituted tertiary propargyl alc. synthesis (up to 52% ee) is also described. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9Related Products of 352655-61-9).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) belongs to chiral phosphine ligands. Many phosphine-catalyzed reactions have been developed for the syntheses of various biologically important acyclic and cyclic molecules. Asymmetric variants of these reactions have evolved relatively slowly. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Related Products of 352655-61-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cyclization of 1,6-Enynes with Aliphatic and Aromatic Alkenes was written by Ueda, Hiroki;Masutomi, Koji;Shibata, Yu;Tanaka, Ken. And the article was included in Organic Letters in 2017.Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) This article mentions the following:

It has been established that a cationic rhodium(I)/(R)-MeO-BIPHEP complex catalyzes the asym. [2 + 2 + 2] cyclization of 1,6-enynes with aliphatic and aromatic alkenes to produce chiral cyclic dienes through β-hydride elimination from rhodacycle intermediates. Thus, obtained chiral cyclic dienes could be converted to chiral spirocompounds without racemization. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Name: (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Enantioface-Selective Palladium-Catalyzed Silaboration of Allenes via Double Asymmetric Induction was written by Suginome, Michinori;Ohmura, Toshimichi;Miyake, Yoshihiro;Mitani, Shin’ichirou;Ito, Yoshihiko;Murakami, Masahiro. And the article was included in Journal of the American Chemical Society in 2003.Computed Properties of C33H25OP This article mentions the following:

Enantioenriched β-borylallylsilanes, e.g., (RO)₂BC(:CH₂)CH(SiMe₂Ph)CH₂CH₂Ph [(RO)₂B = 4,5-diorgano-1,3,2-dioxaborolanyl], were synthesized by Pd-catalyzed enantioface-selective addition of the Si-B bond of chiral 2-dimethylsilyl-4,5-diorgano-1,3,2-dioxaborolane (e.g., organo = Me, Ph, CO₂Prⁱ) to terminal allenes, CH₂:C:CHCH₂CH₂Ph, using a Pd catalyst possessing a chiral monodentate phosphine ligand, e.g., CpPd(allyl)/PPh₃. Use of a silylborane bearing a chiral auxiliary on the B atom was beneficial to gain enantioface selectivities ≤96% de. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Computed Properties of C33H25OP).

(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Computed Properties of C33H25OP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium-catalysed intramolecular asymmetric cyclohydroaryloxycarbonylation of 2-allylphenol derivatives. Synthesis of chiral lactones via cyclocarbonylation was written by Abu Seni, Anas;Kollar, Laszlo;Pongracz, Peter. And the article was included in Molecular Catalysis in 2020.Related Products of 37002-48-5 This article mentions the following:

Homogeneous catalytic hydroaryloxycarbonylation of 2-allylphenol derivatives I (R¹ = H, CH₃, OCH₃, CHO; R² = H, COCH₃) was performed using palladium complexes toward the corresponding lactones II, III, IV. Reactions were conducted under carbon monoxide atm. in the absence of hydrogen gas. Palladium catalyst was generated in situ, using various phosphine ligands e.g., (4S,5S)-4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane and precursors as Pd(OAc)₂, PdCl₂, PdCl₂(PhCN)₂, etc. in the presence of acid additives as HCl, HCOOH, TsOH, etc. In general, chiral 6- III and achiral 7-membered lactones IV were formed dominantly, only trace amounts of the 5-membered lactone II can be identified. Moderate or good enantioselectivity can be achieved using chiral ligands regarding the 6-membered chromanone derivatives III. The regioselectivity of the reaction is particularly effected by catalyst composition and acid co-catalysts and found to be insensitive for substrate substitution. In the experiment, the researchers used many compounds, for example, (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5Related Products of 37002-48-5).

(((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Related Products of 37002-48-5

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Compromise between conjugation length and charge-transfer in nonlinear optical η⁵-monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands: Synthesis, electrochemical studies and first hyperpolarizabilities was written by Garcia, M. Helena;Mendes, Paulo J.;Robalo, M. Paula;Dias, A. Romao;Campo, Jochen;Wenseleers, Wim;Goovaerts, Etienne. And the article was included in Journal of Organometallic Chemistry in 2007.Recommanded Product: 37002-48-5 This article mentions the following:

A series of half-sandwich η⁵-cyclopentadienyliron(II) diphosphine complexes with substituted oligo-thiophene carbonitrile ligands, [FeCp(P-P)(NC{SC₄H₂}_nNO₂)][PF₆] (1a–3a, P-P = dppe; 1b–3b, P-P = (+)-diop; n = 1-3) was prepared by complexation of the nitrile ligands to the corresponding iodides, [FeCp(P-P)I]. The electrochem. behavior of the new compounds was explored by cyclic voltammetry. The compounds 1–3 exhibit pos. solvatochromism, i.e., a bathochromic shift in more polar solvents. Quadratic hyperpolarizabilities (β) of the complexes with dppe co-ligands have been determined by hyper-Rayleigh scattering (HRS) measurements at two fundamental wavelengths of 1.064 and 1.550 μm, to uncover the two-photon resonance effect and to estimate static β values. The obtained overall results are found to be better than for the related η⁵-monocyclopentadienyliron(II) complexes with p-benzonitrile derivatives Although an increase of the resonant β at 1.064 μm with increasing number of thiophene units in the conjugated ligand was found (up to 910 × 10^-30 esu), the static values β₀ remain practically unchanged, as shown by the 1.550 μm measurements. Combined with the electrochem. and spectroscopic data (IR, NMR, UV-vis), this remarkable evolution of β shows that the increase of conjugation length is balanced by a decrease in charge-transfer efficiency. In the experiment, the researchers used many compounds, for example, (((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5Recommanded Product: 37002-48-5).

(((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5) belongs to chiral phosphine ligands. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Recommanded Product: 37002-48-5

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Total synthesis of the antimalarial naphthylisoquinoline alkaloid 5-epi-4′-O-demethylancistrobertsonine C by asymmetric Suzuki cross-coupling was written by Bringmann, Gerhard;Ruedenauer, Stefan;Bruhn, Torsten;Benson, Lauren;Brun, Reto. And the article was included in Tetrahedron in 2008.COA of Formula: C26H28FeNP This article mentions the following:

The first total synthesis of the antimalarial naphthylisoquinoline alkaloid 5-epi-4′-O-demethylancistrobertsonine C (I) and its-as yet unnatural-atropo-diastereomer is described. The key step of the synthesis is the construction of the rotationally hindered and thus stereogenic biaryl axis, which was built up by a Suzuki reaction. The use of chiral ligands in the palladium-catalyzed cross-coupling permitted to increase the low internal asym. induction up to a diastereomeric ratio of 74:26. The assignment of the axial configurations of the atropo-diastereomers was achieved by 2D NMR experiments and corroborated by quantum chem. CD calculations In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2COA of Formula: C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. Many phosphine-catalyzed reactions have been developed for the syntheses of various biologically important acyclic and cyclic molecules. Asymmetric variants of these reactions have evolved relatively slowly. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.COA of Formula: C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Ligand-Substrate Dispersion Facilitates the Copper-Catalyzed Hydroamination of Unactivated Olefins was written by Lu, Gang;Liu, Richard Y.;Yang, Yang;Fang, Cheng;Lambrecht, Daniel S.;Buchwald, Stephen L.;Liu, Peng. And the article was included in Journal of the American Chemical Society in 2017.Category: chiral-phosphine-ligands This article mentions the following:

The current understanding of ligand effects in transition metal catalysis is mostly based on the anal. of catalyst-substrate through-bond and through-space interactions, with the latter commonly considered to be repulsive in nature. The dispersion interaction between the ligand and the substrate, a ubiquitous type of attractive noncovalent interaction, is seldom accounted for in the context of transition-metal-catalyzed transformations. Herein we report a computational model to quant. analyze the effects of different types of catalyst-substrate interactions on reactivity. Using this model, we show that in the copper(I) hydride (CuH)-catalyzed hydroamination of unactivated olefins, the substantially enhanced reactivity of copper catalysts based on bulky bidentate phosphine ligands originates from the attractive ligand-substrate dispersion interaction. These computational findings are validated by kinetic studies across a range of hydroamination reactions using structurally diverse phosphine ligands, revealing the critical role of bulky P-aryl groups in facilitating this process. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9Category: chiral-phosphine-ligands).

(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis