Chiral phosphine ligands

Practical Synthesis of MDM2 Antagonist RG7388. Part 1: A Cu(II)-Catalyzed Asymmetric [3 + 2] Cycloaddition was written by Shu, Lianhe;Gu, Chen;Fishlock, Dan;Li, Zizhong. And the article was included in Organic Process Research & Development in 2016.Computed Properties of C38H32O2P2 This article mentions the following:

An efficient asym. synthesis of MDM2 antagonist RG7388 (I) is reported. The highly functionalized chiral pyrrolidine carboxamate was assembled via a Cu(OAc)₂/(R)-BINAP catalyzed asym. [3+2] cycloaddition, which gave the exo and endo adducts in a ratio of 10:1, with high enantiomeric excess for the exo isomer. A one pot hydrolysis and retro-Mannich/Mannich isomerization of the cycloaddition adducts in the presence of aqueous sodium hydroxide afforded RG7388 in high chem. and enantiomeric purities and 69% overall yield. In the experiment, the researchers used many compounds, for example, (R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1Computed Properties of C38H32O2P2).

(R)-(6,6′-Dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine) (cas: 133545-16-1) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Computed Properties of C38H32O2P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Cu(I)-Ming-phos Catalyzed Enantioselective [3+2] Cycloadditions of Glycine ketimines to β-Trifluoromethyl Enones was written by Liu, Bing;Zhang, Zhan-Ming;Xu, Bing;Xu, Shan;Wu, Hai-Hong;Zhang, Junliang. And the article was included in Advanced Synthesis & Catalysis in 2018.Related Products of 2222798-18-5 This article mentions the following:

A catalytic asym. [3+2] cycloaddition of glycine ketimines with β-CF₃ β,β-disubstituted enones was realized in the presence of a chiral copper(I)/Ming-Phos complex. This method provided an access to construct highly functionalized pyrrolidines e.g.,I, bearing three contiguous stereocenters, which including a trifluoromethylated all-carbon quaternary stereocenter. The features of this reaction included high chemo-, diastereo-, enantioselectivity (up to > 20:1 cr, > 20:1 dr, 98% ee), readily available starting materials, well functional-group tolerance and mild reaction conditions. Control experiments demonstrated that the fluoro-substituent was crucial for the reactivity. In the experiment, the researchers used many compounds, for example, (R)-N-((R)-(2-(Diphenylphosphino)phenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide (cas: 2222798-18-5Related Products of 2222798-18-5).

(R)-N-((R)-(2-(Diphenylphosphino)phenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide (cas: 2222798-18-5) 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. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Related Products of 2222798-18-5

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Achieving Chemo-, Regio-, and Stereoselectivity in Palladium-Catalyzed Reaction of γ-Borylated Allylic Acetates was written by Kukkadapu, Krishna Kishore;Ouach, Aziz;Lozano, Pedro;Vaultier, Michel;Pucheault, Mathieu. And the article was included in Organic Letters in 2011.Reference of 174810-09-4 This article mentions the following:

Three-carbon highly functionalized γ-borylated allylic acetates underwent a regio- and stereocontrolled Tsuji-Trost reaction in the presence of palladium complexes. An ipso substitution of the acetate with complete stereoretention of the chiral center was achieved, leading to vinylic boronates with enantiomeric excesses above 99%. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Reference of 174810-09-4).

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) 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. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Reference of 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric Rh(I)-catalyzed intramolecular [3 + 2] cycloaddition of 1-yne-vinylcyclopropanes for bicyclo[3.3.0] compounds with a chiral quaternary carbon stereocenter and density functional theory study of the origins of enantioselectivity was written by Lin, Mu;Kang, Guan-Yu;Guo, Yi-An;Yu, Zhi-Xiang. And the article was included in Journal of the American Chemical Society in 2012.Category: chiral-phosphine-ligands This article mentions the following:

A highly enantioselective Rh(I)-catalyzed intramol. [3 + 2] cycloaddition of 1-yne-VCPs to bicyclo[3.3.0] compounds with an all-carbon chiral quaternary stereocenter at the bridgehead carbon was developed. DFT calculations of the energy surface of the catalytic cycle (complexation, cyclopropane cleavage, alkyne insertion, and reductive elimination) of the asym. [3 + 2] cycloaddition reaction indicated that the rate- and stereo-determining step is the alkyne-insertion step. Anal. of the alkyne-insertion transition states revealed that the serious steric repulsion between the substituents in the alkyne moiety of the substrates and the rigid H₈-BINAP backbone is responsible for not generating the disfavored [3 + 2] cycloadducts. 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: 37002-48-5Category: chiral-phosphine-ligands).

(((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. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Iridium Catalysts with f-Amphox Ligands: Asymmetric Hydrogenation of Simple Ketones was written by Wu, Weilong;Liu, Shaodong;Duan, Meng;Tan, Xuefeng;Chen, Caiyou;Xie, Yun;Lan, Yu;Dong, Xiu-Qin;Zhang, Xumu. And the article was included in Organic Letters in 2016.COA of Formula: C26H28FeNP This article mentions the following:

A series of modular and rich electronic tridentate ferrocene aminophosphoxazoline ligands (f-amphox) have been successfully developed and used in iridium-catalytic asym. hydrogenation of simple ketones to afford corresponding enantiomerically enriched alcs. under mild conditions with superb activities and excellent enantioselectivities (up to 1,000,000 TON, almost all products up to >99% ee, full conversion). The resulting chiral alcs. and their derivatives are important intermediates in pharmaceuticals. 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. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.COA of Formula: C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Defined rhodium-MandyPhos pre-catalyst systems was written by Nass, Andreas Rivas;Doppiu, Angelino;Karch, Ralf;Schuster, Andreas;Stephen, A.;Hashmi, K.. And the article was included in Chimica Oggi in 2009.Reference of 174467-31-3 This article mentions the following:

Investigations of Ru- and Rh-based chiral hydrogenation reactions using the ligands MandyPhos and TaniaPhos are up to now based on in situ protocols. The purpose of this and prior work was the clear and detailed structural description of isolated rhodium and ruthenium pre-catalysts with these ligands in order to develop defined ready to use catalytic systems for asym. synthesis. In the case of ruthenium it was found that it is possible to isolate and identify well-defined pre-catalyst systems only by establishing new protocols for complex synthesis. Driven by those experiences, the coordination behavior of MandyPhos with rhodium was investigated and a similar picture emerged. This study provides new synthetic routes to stable rhodium complexes with MandyPhos ligands and norbornadiene or cyclooctadiene ancillary ligands. In the experiment, the researchers used many compounds, for example, (R,R)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-bis(diphenylphosphino)ferrocene (cas: 174467-31-3Reference of 174467-31-3).

(R,R)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-bis(diphenylphosphino)ferrocene (cas: 174467-31-3) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Reference of 174467-31-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B was written by Trost, Barry M.;Malhotra, Sushant;Chan, Walter H.. And the article was included in Journal of the American Chemical Society in 2011.Recommanded Product: 174810-09-4 This article mentions the following:

Pd-catalyzed asym. prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl products, e.g. I and II, has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Addnl., control of the regio- and diastereoselectivity was obtained using π-geranylpalladium complexes. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Recommanded Product: 174810-09-4).

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. Recommanded Product: 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Cobalt-Catalyzed Asymmetric Addition of Silylacetylenes to 1,1-Disubstituted Allenes was written by Sawano, Takahiro;Ou, Keiyu;Nishimura, Takahiro;Hayashi, Tamio. And the article was included in Journal of Organic Chemistry in 2013.Product Details of 360048-63-1 This article mentions the following:

The asym. addition of silylacetylenes to 1,1-disubstituted allenes proceeded in the presence of a Co/chiral bisphosphine ligand to give the corresponding enynes with high enantioselectivity. E.g., reaction of (4-MeOC₆H₄)CMe:C:CH₂ with ⁱPr₃SiCCH in the presence of 5 mol% Co(OAc)₂·4H₂O/5 mol% dppe/50 mol% Zn in DMSO at 80° gave 89% yield of (4-MeOC₆H₄)CHMeC(:CH₂)CCSiⁱPr₃ (major isomer). The results of D-labeling experiments indicated that a H atom at the chiral center is originated from the terminal alkyne, and they were in good agreement with the proposed catalytic cycle where enantioselectivity is determined by the reaction of the proposed π-allylcobalt intermediate with the terminal alkyne. In the experiment, the researchers used many compounds, for example, (1R)-1-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene (cas: 360048-63-1Product Details of 360048-63-1).

(1R)-1-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2-[(1R)-1-(dicyclohexylphosphino)ethyl]ferrocene (cas: 360048-63-1) 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. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Product Details of 360048-63-1

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Novel 1,4-diphosphanes with imidazolidin-2-one backbones as chiral ligands: highly enantioselective Rh-catalyzed hydrogenation of enamides was written by Lee, Sang-Gi;Zhang, Yong Jian;Song, Choong Eui;Lee, Jae Kyun;Choi, Jung Hoon. And the article was included in Angewandte Chemie, International Edition in 2002.Category: chiral-phosphine-ligands This article mentions the following:

Asym. hydrogenation of N-acetyl α-aryl enamides ArC(:CHR¹)NHAc [Ar = (un)substituted Ph; R¹ = H, Me, Et] was catalyzed by [Rh(cod)₂]BF₄ and 1,4-diphosphane ligands I (R = H, Me, Et, etc.). I were prepared from a L-tartaric acid derivative 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: 37002-48-5Category: chiral-phosphine-ligands).

(((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene))bis(diphenylphosphine) (cas: 37002-48-5) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Cascade CuH-catalyzed conversion of alkynes into enantioenriched 1,1-disubstituted products was written by Gao, De-Wei;Gao, Yang;Shao, Huiling;Qiao, Tian-Zhang;Wang, Xin;Sanchez, Brittany B.;Chen, Jason S.;Liu, Peng;Engle, Keary M.. And the article was included in Nature Catalysis in 2020.HPLC of Formula: 352655-61-9 This article mentions the following:

Enantioenriched α-aminoboronic acids play a unique role in medicinal chem. and have emerged as privileged pharmacophores in proteasome inhibitors. Addnl., they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asym. alkene hydrofunctionalization has become a powerful tool to construct stereogenic C centers. By contrast, applying CuH cascade catalysis to achieve the reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, synthetic challenge. Herein, the authors report an efficient strategy to synthesize α-aminoboron compounds by a CuH-catalyzed hydroboration/hydroamination cascade of readily available alkynes. Notably, this transformation selectively delivers the desired 1,1-heterodifunctionalized product rather than the alternative homodifunctionalized, 1,2-heterodifunctionalized or reductively monofunctionalized byproducts, thereby offering rapid access to these privileged scaffolds with high chemo-, regio- and enantioselectivity. 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: 352655-61-9HPLC of Formula: 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. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Effective chiral catalysts for nucleophilic phosphine catalysis are scarce, seriously limiting the development of asymmetric variants. HPLC of Formula: 352655-61-9

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis