Category: 174810-09-4

A new preparation of homochiral N-protected 5-hydroxy-3-piperidenes, promising chiral building blocks, by palladium-catalyzed deracemization of their alkyl carbonates was written by Takahata, Hiroki;Suto, Yumiko;Kato, Erina;Yoshimura, Yuichi;Ouchi, Hidekazu. And the article was included in Advanced Synthesis & Catalysis in 2007.Application of 174810-09-4 This article mentions the following:

The Pd-catalyzed deracemization of N-protected alkyl carbonates of 5-hydroxy-3-piperidenes (e.g. N-(p-tolylsulfonyl)-5-(methoxycarbonyloxy)-1,2,5,6-tetrahydropyridine) using chiral phosphine ligands is described. A Trost ligand such as (R)-BPA ((1R,2R)-1,2-bis[[2-(diphenylphosphino)benzoyl]amino]cyclohexane) is a suitable chiral ligand for the deracemization, providing N-protected 5-hydroxy-3-piperidenes in good yields with good to high enantioselectivities. A plausible mechanism for the reaction is proposed. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Application 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. 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. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Application of 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium-Catalyzed Asymmetric Direct Intermolecular Allylation of α-Aryl Cyclic Vinylogous Esters: Divergent Synthesis of (+)-Oxomaritidine and (-)-Mesembrine was written by Wang, Wei;Dai, Jun;Yang, Qiqiong;Deng, Yu-Hua;Peng, Fangzhi;Shao, Zhihui. And the article was included in Organic Letters in 2021.Application of 174810-09-4 This article mentions the following:

We demonstrate that α-aryl cyclic vinylogous esters are competent substrates in the direct intermol. Pd-catalyzed asym. allylic alkylation, enabling a straightforward enantioselective synthesis of 6-allyl-6-aryl-3-ethoxycyclohex-2-en-1-ones, common motifs embedded in numerous structurally diverse natural products. As an initial demonstration of the utility of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (-)-mesembrine have been completed divergently. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Application 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. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Application of 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium Catalyzed Kinetic and Dynamic Kinetic Asymmetric Transformations of γ-Acyloxybutenolides. Enantioselective Total Synthesis of (+)-Aflatoxin B₁ and B_2a was written by Trost, Barry M.;Toste, F. Dean. And the article was included in Journal of the American Chemical Society in 2003.Related Products of 174810-09-4 This article mentions the following:

The reaction of γ-tert-butoxycarbonyloxy-2-butenolide with phenol nucleophiles in the presence of a Pd(0) complex with chiral ligands may be performed under conditions that favor either a kinetic resolution or a kinetic asym. transformation (KAT) or dynamic kinetic asym. transformation (DYKAT). Performing the reaction at high concentration (0.5 M) in the presence of a carbonate base favors the former, i.e., KAT; whereas, running the reaction at 0.1M in the presence of tetra-n-butylammonium chloride favors the DYKAT process. Syntheses of aflatoxin B₁ (I) and B_2a (II) employs the DYKAT to introduce the stereochem. Starting with Pechmann condensation of the monomethyl ether of phloroglucinol, the requisite phenol nucleophile is constructed in two steps. The DYKAT proceeds with > 95% ee. A reductive Heck cyclization followed by a lanthanide catalyzed intramol. acylation completes the synthesis of the pentacyclic nucleus in 3 steps. Reduction of the lactone provides aflatoxin B_2a and its dehydration product B₁. This synthetic strategy creates an asym. synthesis of the former in only 7 steps and the latter in 9 steps. Thus, the ultimate synthetic sequence involves butenolide III (Boc = CO₂CMe₃) and 5-methoxybenzene-1,3-diol via pyranones IV (X = H, I), butenolide V, and furofuranones VI, VII and VIII, giving II and then I. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Related Products 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. 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 ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Related Products of 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates was written by Starkov, Pavel;Moore, Jared T.;Duquette, Douglas C.;Stoltz, Brian M.;Marek, Ilan. And the article was included in Journal of the American Chemical Society in 2017.Synthetic Route of C52H44N2O2P2 This article mentions the following:

Authors report a divergent and modular protocol for the preparation of acyclic mol. frameworks containing newly created quaternary carbon stereocenters. Central to this approach is a sequence composed of a (1) regioselective and -retentive preparation of allyloxycarbonyl-trapped fully substituted stereodefined amide enolates and of a (2) enantioselective palladium-catalyzed decarboxylative allylic alkylation reaction using a novel bisphosphine ligand. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Synthetic Route of C52H44N2O2P2).

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) 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 ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Synthetic Route of C52H44N2O2P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Catalytic enantioselective addition of phenylboronic acid and phenylboroxine to N-tosylimines: Pd^II and Rh^I catalysis was written by Marques, Carolina S.;Burke, Anthony J.. And the article was included in European Journal of Organic Chemistry in 2010.COA of Formula: C52H44N2O2P2 This article mentions the following:

This is the first account of a successful, Pd^II-catalyzed enantioselective addition of phenylboronic acid to electron-deficient N-tosylarylimines by using chiral diphosphane ligands. A number of com. diphosphane ligands were screened. Despite moderate to good yields, ee values of 99% could be achieved with MeDuPhos. Novel Rh^I catalysts were also screened, and ee values as high as 74% could be obtained. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4COA of Formula: C52H44N2O2P2).

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) 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: C52H44N2O2P2

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

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

Palladium-catalyzed DYKAT of vinyl epoxides: Enantioselective total synthesis and assignment of the configuration of (+)-broussonetine G was written by Trost, Barry M.;Horne, Daniel B.;Woltering, Michael J.. And the article was included in Angewandte Chemie, International Edition in 2003.HPLC of Formula: 174810-09-4 This article mentions the following:

A potential general approach to potent N-heterocyclic glycosidase inhibitors is illustrated by the first total synthesis of (+)-broussonetine G. The key transformation of the synthesis relies on two successive palladium-catalyzed asym. allylic alkylations of butadiene monoxide with a nitrogen nucleophile to construct the pyrrolidine core. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4HPLC of Formula: 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. 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.HPLC of Formula: 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Access to trans-3,4-Dihydroxy-2-alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic N,O-Acetals as a Diversity-Generating Element was written by Kang, Soyeong;Kim, Dong-gil;Rhee, Young Ho. And the article was included in Chemistry – A European Journal in 2014.Quality Control of N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) This article mentions the following:

A highly efficient and stereoselective synthetic pathway towards trans-3,4-dihydroxy-2-alkylpyrrolidines and piperidines I (n = 1, 2; A = CO, C(C₂H₅)₂; R = CH₂COPh, CH₂CCH, CN, etc.) is described. The nature of the protecting groups on the hydroxyl moieties played a crucial role on the trans selectivity. By using this method, a concise total synthesis of (-)-2-epilentiginosine has been achieved. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Quality Control of N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)).

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. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Quality Control of N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide)

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Palladium-catalyzed DYKAT of butadiene mono-epoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G was written by Trost, Barry M.;Horne, Daniel B.;Woltering, Michael J.. And the article was included in Chemistry – A European Journal in 2006.SDS of cas: 174810-09-4 This article mentions the following:

Palladium catalyzed DYKAT (dynamic kinetic asym. transformation) allylic alkylation reaction of an amine with two equivalent of butadiene monoxide allows for the expedient synthesis of trans- and cis-2,5-dihydropyrroles. The versatility of these chiral synthons towards the synthesis of a wide variety of imino-sugar natural products was demonstrated with the short and high yielding asym. syntheses of (+)-DMDP, and (-)-bulgecinine. In addition, the first total synthesis of (+)-broussonetine G, a potent glycosidase inhibitor, is described along with the assignment of its relative and absolute stereochem. configuration. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4SDS of cas: 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. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.SDS of cas: 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis