Tag: 700-800

Quality Control of (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphineOn March 14, 2019, Wei, Xiao-Feng; Wakaki, Takayuki; Itoh, Taisuke; Li, Hong-Liang; Yoshimura, Takayoshi; Miyazaki, Aya; Oisaki, Kounosuke; Hatanaka, Miho; Shimizu, Yohei; Kanai, Motomu published an article in Chem. The article was 《Catalytic Regio- and Enantioselective Proton Migration from Skipped Enynes to Allenes》. The article mentions the following:

Here, a copper(I)-catalyzed enantioselective proton migration from skipped enynes to allenes I [R1 = Ph, 3-MeC6H4, 3-thienyl, etc.; R2 = H, Me, Bn, etc.] as an efficient approach in chiral allene synthesis was reported. With catalyst loading as low as 0.5 mol %, the reaction proceeded smoothly under mild conditions without the need for addnl. stoichiometric reagents or generation of waste. Novel chiral ligand containing diphenylphosphine moiety plays a critical role in furnishing high catalyst activity, promoting regioselective protonation to produce allenes instead of conjugated enynes and inducing axial chirality of allenes. The multiple roles of the chiral ligand were rationalized by d. functional theory calculations In the experimental materials used by the author, we found (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8Quality Control of (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine)

(R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Quality Control of (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine 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

SDS of cas: 1156547-61-3On May 15, 2009 ,《Copper-ClickFerrophos-complex-catalyzed enantioselective reductive aldol reaction》 appeared in Synlett. The author of the article were Kato, Minoru; Oki, Hiroshi; Ogata, Kenichi; Fukuzawa, Shin-ichi. The article conveys some information:

Nonracemic ClickFerrophos (phosphinyltriazolylmethylferrocenylphosphine) ligands I (R = H, Ph; R1, R2 = Ph2P, Cy2P, dicyclopentylphosphinyl; Cy = cyclohexyl) are prepared as ligands for stereo- and enantioselective reductive aldol addition reactions of acrylates with aryl Me ketones and cyclohexanecarboxaldehyde. In the presence of I (R = Ph; R1 = R2 = Cy2P) and the methanol solvate of FCu(PPh3)3, acetophenones R3COMe (R3 = Ph, 4-FC6H4, 4-ClC6H4, 3-ClC6H4, 4-F3CC6H4, 4-MeOC6H4, 2-thienyl, 3-thienyl) undergo phenylsilane-mediated reductive aldol addition reactions with Me acrylate to give β-hydroxyesters II in 36-93% yields, 90:10-99:1 dr, and in 73-85% ee; the use of other silanes and ligand and the use of additives gives products with reduced diastereoselectivities or enantioselectivities. Phenylsilane-mediated reductive aldol additions of cyclohexanecarboxaldehyde and Me, tert-Bu, and cyclohexyl acrylate in the presence of nonracemic ClickFerrophos ligands give β-hydroxyesters in variable diastereoselectivities and enantioselectivities. In the experiment, the researchers used many compounds, for example, (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3SDS of cas: 1156547-61-3)

(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. SDS of cas: 1156547-61-3 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

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

《Domino Asymmetric Conjugate Addition-Conjugate Addition》 was written by Germain, Nicolas; Schlaefli, Doriane; Chellat, Mathieu; Rosset, Stephane; Alexakis, Alexandre. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene And the article was included in Organic Letters on April 4 ,2014. The article conveys some information:

In the presence of copper catalysts and nonracemic phosphoramidite, imidazolium, or aminoferrocenylphosphine ligands, ethylmagnesium bromide, trimethylaluminum, and dimethyl- and diethylzinc underwent enantioselective and diastereoselective conjugate addition reactions to cyclopentenones, cyclohexenones, and cycloheptenones followed by trapping with either nitroalkenes or 1,1-bis(phenylsulfonyl)ethylene to give oxoalkyl cycloalkanones in 63-85% yields, 57:43-97:3 dr, and in 86->99.5% ee; the oxoalkyl cycloalkanones were converted by various methods to indenones, a hydrazulenone, a tetrahydrobenzofuran and a tetrahydroindole, and an octahydronaphthalene. In the experiment, the researchers used many compounds, for example, (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene)

(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. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Cowan, David J.; Collins, Jon L.; Mitchell, Mark B.; Ray, John A.; Sutton, Peter W.; Sarjeant, Amy A.; Boros, Eric E. published their research in Journal of Organic Chemistry on December 20 ,2013. The article was titled 《Enzymatic- and Iridium-Catalyzed Asymmetric Synthesis of a Benzothiazepinylphosphonate Bile Acid Transporter Inhibitor》.HPLC of Formula: 1156547-61-3 The article contains the following contents:

A synthesis of the benzothiazepine phosphonic acid 3 (shown as I), employing both enzymic and transition metal catalysis, is described. The quaternary chiral center of 3 was obtained by resolution of Et (2-ethyl)norleucinate (4) with porcine liver esterase (PLE) immobilized on Sepabeads. The resulting (R)-amino acid (H2N)(HOOC)C(Bu)(Et) (5) was converted in two steps to aminosulfate (Bu)(Et)C(NH2)(CH2OSO3) (7), which was used for construction of the benzothiazepine ring. Benzophenone, 2-benzoyl-5-(bromomethyl)-4-methoxyphenyl trifluoromethanesulfonate (15), prepared in four steps from trimethylhydroquinone, 1,4-(MeO)2-2-MeC6H3 (11), enabled sequential incorporation of P (Arbuzov chem.) and S (Pd(0)-catalyzed thiol coupling) leading to mercaptan intermediate, di-Et 4-benzoyl-5-mercapto-2-methoxybenzylphosphonate (18). S-Alkylation of 18 with aminosulfate 7 followed by cyclodehydration afforded the corresponding dihydrobenzothiazepine. Ir-catalyzed asym. hydrogenation of this dihydrobenzothiazepine with the complex of [Ir(COD)2BArF] (26, BArF = [B(C6H3(CF3)2-3,5)4]) and Taniaphos ligand afforded the corresponding (3R,5R)-tetrahydrobenzothiazepine following flash chromatog. Oxidation of the tetrahydrobenzothiazepine to the corresponding sulfone and phosphonate hydrolysis completed the synthesis of 3 in 12 steps and 13% overall yield. The results came from multiple reactions, including the reaction of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3HPLC of Formula: 1156547-61-3)

(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. HPLC of Formula: 1156547-61-3 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

In 2018,Angewandte Chemie, International Edition included an article by Itoh, Taisuke; Kanzaki, Yamato; Shimizu, Yohei; Kanai, Motomu. Recommanded Product: (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine. The article was titled 《Copper(I)-catalyzed enantio- and diastereodivergent borylative coupling of styrenes and imines》. The information in the text is summarized as follows:

We report copper(I)-catalyzed enantio- and diastereodivergent borylative coupling of styrenes Ar1CH:CH2 with imines RCH:HP(S)Ar22 and B2pin2 to produce enantiomerically-enriched α,β-dibranched γ-boryl amine derivatives RCH(NHPSAr22)CHAr1CH2Bpin (3). Each of the four possible stereoisomers of the products, derived from the two contiguous stereocenters, was selectively accessible by choosing a proper chiral ligand for the copper catalyst. This method, which combines catalyst-controlled stereodivergency and constitutional divergency derived from the lynchpin motif (i.e., the C-B bond), offers a strategy for addressing the construction of mol. structural diversity concomitant with precise chirality control. The results came from multiple reactions, including the reaction of (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8Recommanded Product: (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine)

(R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine(cas: 849924-49-8) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. Recommanded Product: (R)-1-{(R)-2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]ferrocenyl}-ethylbis(2-methylphenyl)phosphine 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 《Highly enantioselective copper(I)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones》 were Sanz-Marco, Amparo; Blay, Gonzalo; Munoz, M. Carmen; Pedro, Jose R.. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2015. Name: (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene The author mentioned the following in the article:

The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol%) of a copper(I)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne. Pre-metalation of the terminal 1,3-diyne with stoichiometric or higher amounts of dialkylzinc reagent is not required. The corresponding internal diynes bearing a propargylic stereogenic center are obtained with good yields and excellent enantioselectivities. The experimental part of the paper was very detailed, including the reaction process of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Name: (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene)

(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. Name: (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Brewitz, Lennart; Arteaga, Fernando Arteaga; Yin, Liang; Alagiri, Kaliyamoorthy; Kumagai, Naoya; Shibasaki, Masakatsu published their research in Journal of the American Chemical Society on December 23 ,2015. The article was titled 《Direct Catalytic Asymmetric Mannich-Type Reaction of α- and β-Fluorinated Amides》.Computed Properties of C43H63FeNP2 The article contains the following contents:

The last two decades have witnessed the emergence of direct enolization protocols providing atom-economical and operationally simple methods to use enolates for stereoselective C-C bond-forming reactions, eliminating the inherent drawback of the preformation of enolates using stoichiometric amounts of reagents. In its infancy, direct enolization relied heavily on the intrinsic acidity of the latent enolates, and the reaction scope was limited to readily enolizable ketones and aldehydes. Recent advances in this field enabled the exploitation of carboxylic acid derivatives for direct enolization, offering expeditious access to synthetically versatile chiral building blocks. Despite the growing demand for enantioenriched fluorine-containing small mols., α- and β-fluorinated carbonyl compounds have been neglected in direct enolization chem. because of the competing and dominating defluorination pathway. Herein we present a comprehensive study on direct and highly stereoselective Mannich-type reactions of α- and β-fluorine-functionalized 7-azaindoline amides that rely on a soft Lewis acid/hard Bronsted base cooperative catalytic system to guarantee an efficient enolization while suppressing undesired defluorination. This protocol contributes to provide a series of fluorinated analogs of enantioenriched β-amino acids for medicinal chem.(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Computed Properties of C43H63FeNP2) was used in this study.

(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