Chiral phosphine ligands

In 2017,Chemistry – A European Journal included an article by Zhang, Wanli; Ma, Shengming. Recommanded Product: 256390-47-3. The article was titled 《Palladium-Catalyzed Enantioselective Alkoxycarbonylation of Propargylic Carbonates with (R)- or (S)-3,4,5-(MeO)3-MeOBIPHEP》. The information in the text is summarized as follows:

(R)- and (S)-3,4,5-(MeO)3-MeOBIPHEP were identified as the efficient chiral ligands for the Pd-catalyzed highly enantioselective synthesis of 2,3-allenoates from different types of easily available racemic propargylic carbonates with 90-98% ee and decent yields. The potential of the products was demonstrated with high chirality transfer efficiency. 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: 256390-47-3Recommanded Product: 256390-47-3) 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. Recommanded Product: 256390-47-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Pd-Catalyzed asymmetric [5 + 2] cycloaddition of vinylethylene carbonates and cyclic imines: access to N-fused 1,3-oxazepines》 was written by Ahn, Hye-In; Park, Jong-Un; Xuan, Zi; Kim, Ju Hyun. SDS of cas: 210169-54-3 And the article was included in Organic & Biomolecular Chemistry in 2020. The article conveys some information:

A Pd-catalyzed asym. [5 + 2] cycloaddition reaction was developed for the synthesis of N-fused 1,3-oxazepines using vinylethylene carbonates and sulfamate-derived cyclic imines. Under mild reaction conditions, a series of optically active N-fused 1,3-oxazepines were synthesized in good yields (up to 89%) and enantioselectivities (up to 90 : 10 er), indicating this method as a straightforward approach to enantiomerically enriched 1,3-oxazepine derivatives The synthetic utility of the presented reaction was further demonstrated by the successful transformation of the resulting 1,3-oxazepines to useful polycyclic N-fused 1,3-oxazepanes. In the experiment, the researchers used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3SDS of cas: 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 aldehydesSDS of cas: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Shi, Zhanglin; Shen, Chaoren; Dong, Kaiwu published an article in 2021. The article was titled 《Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones》, and you may find the article in Chemistry – A European Journal.Category: chiral-phosphine-ligands The information in the text is summarized as follows:

Palladium-catalyzed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed. In the part of experimental materials, we found many familiar compounds, such as (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Category: chiral-phosphine-ligands)

(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.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Electric Literature of C50H56O14P2On June 5, 2015, Murai, Masahito; Takeshima, Hirotaka; Morita, Haruka; Kuninobu, Yoichiro; Takai, Kazuhiko published an article in Journal of Organic Chemistry. The article was 《Acceleration effects of phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds》. The article mentions the following:

The current work describes the marked rate of acceleration caused by phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds. The reactivity was affected by the steric and electronic nature of the phosphine ligands. The use of the bulky and electron-rich diphosphine ligand (R)-DTBM-SEGPHOS was highly effective to yield the dehydrogenative silylation products selectively in the presence of a hydrogen acceptor. An appropriate choice of C2-sym. chiral diphosphine ligand enables the asym. dehydrogenative silylation via the enantioselective desymmetrization of the C(sp3)-H bond. The unprecedented catalytic germylation of C(sp3)-H bonds with dehydrogenation was also examined with the combination of the rhodium complex and a wide bite angle diphosphine ligand to provide the corresponding 2,3-dihydrobenzo[b]germoles in good yield. 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

In 2019,Organic & Biomolecular Chemistry included an article by Wang, Kaiye; Xiang, Yanan; Shi, Zhujun; Wang, Hongyu; Li, Na; Tang, Bo. Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine. The article was titled 《Asymmetric kinetic resolution of sulfides for the construction of unsymmetric sulfides and chiral 3,3-disubstituted oxindoles》. The information in the text is summarized as follows:

An enantioselective method was developed for the synthesis of unsym. disulfides R’SSR” [R’ = allyl, CH2CO2Me, Bn, etc.; R” = 4-FC6H4, 4-BrC6H4, Bn] and chiral 3,3-disubstituted oxindoles I [R1 = allyl, 4-BrC6H4, Bn, etc.; X = H, 5-Br, 5-I, 6-Br; R2 = Me, PMB] in one step from oxindoles and thiols using chiral phosphines catalyst. Many substituted thiols and 3,3-disubstituted oxindoles were well tolerated and produced high yields and enantioselectivities under mild conditions. In the experimental materials used by the author, we found (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Saitoh, Akihito; Achiwa, Kazuo; Tanaka, Kiyoshi; Morimoto, Toshiaki published an article in Journal of Organic Chemistry. The title of the article was 《Versatile Chiral Bidentate Ligands Derived from α-Amino Acids: Synthetic Applications and Mechanistic Considerations in the Palladium-Mediated Asymmetric Allylic Substitutions》.HPLC of Formula: 286454-86-2 The author mentioned the following in the article:

A new class of chiral amidine-phosphine hybrid ligands which are readily accessible from the corresponding α-amino acids was developed. A versatility for construction of new ligands is desirable, by which a variety of reactions and substrates become applicable. Indeed, a variety of modifications, such as exchange reactions to other amino groups in the amidine skeleton and the production of other types of ligands, are possible using the precursor compounds Thus, novel chiral ligands which provide sterically and electronically different chiral circumstances were prepared and used for the palladium-mediated asym. allylic substitutions of both acyclic and cyclic compounds In these reactions, high levels of asym. induction were achieved for both substrates. A marked advancement of reactivity and enantioselectivity in palladium-catalyzed asym. allylations of 1,3-diphenylpropen-2-yl pivalate (14a) was attained by examination of electronic substituent effects in a new series of chiral P-N and S-N hybrid ligands. Mechanistic views concerning the enantiodiscriminating step were demonstrated, in which a good correlation between a novel Pr/Mr concept and the absolute configuration of allylation products are discussed for the prediction of enantioselecting direction. The use of ketene silyl acetals as nucleophiles was investigated and compared with the corresponding harder anionic carbon nucleophiles. The former nucleophiles afforded higher enantioselectivity in asym. allylic transformations of 14a. The experimental part of the paper was very detailed, including the reaction process of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2HPLC of Formula: 286454-86-2)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.HPLC of Formula: 286454-86-2 This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2018,Bora, Pranjal P.; Sun, Gui-Jun; Zheng, Wei-Feng; Kang, Qiang published 《Rh/Lewis Acid Catalyzed Regio-, Diastereo- and Enantioselective Addition of 2-Acyl Imidazoles with Allenes》.Chinese Journal of Chemistry published the findings.Synthetic Route of C38H28O4P2 The information in the text is summarized as follows:

A highly regio-, diastereo- and enantioselective addition of 2-acyl imidazoles or 2-acyl pyridines with allenes promoted by Rh/Lewis acid synergistically catalytic system was described. This atom economic approach led to the formation of the branched allylic alkylated products including acyclic quaternary all-carbon stereogenic centers in good yields with good to excellent diastereo- and enantioselectivities. Kinetic studies revealed that the rate-determining step in this process was the oxidative addition of Rh(I) with C-H bond. The results came from multiple reactions, including the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Synthetic Route 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.Synthetic Route of C38H28O4P2

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

Cadart, Timothee; Necas, David; Kaiser, Reinhard P.; Favereau, Ludovic; Cisarova, Ivana; Gyepes, Robert; Hodacova, Jana; Kalikova, Kveta; Bednarova, Lucie; Crassous, Jeanne; Kotora, Martin published their research in Chemistry – A European Journal in 2021. The article was titled 《Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes》.Synthetic Route of C38H28O4P2 The article contains the following contents:

The enantioselective synthesis of chiral [7]-helical dispirodihydro[2,1-c]indenofluorenes (DSF-IFs) was achieved for the first time in good yields with high er values (er up to 99 : 1). The crucial step of the whole reaction sequence was the enantioselective intramol. [2+2+2] cycloaddition of tethered triynediols to indenofluorenediols, which was catalyzed by a Rh/SEGPHOS complex. Further transformations led to the corresponding DSF-IFs. The prepared helically chiral DSF-IFs combine circularly polarized luminescence (CPL) activity (glum=∼10-3) with exceptionally high fluorescence quantum yields (up to Φlum=0.97). In the part of experimental materials, we found many familiar compounds, such as (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Synthetic Route of C38H28O4P2)

(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.Synthetic Route of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Low-pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes》 was written by Movahhed, Sohajl; Westphal, Julia; Dindaroglu, Mehmet; Falk, Anna; Schmalz, Hans-Guenther. Reference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleThis research focused onvinylarene ethene cobalt catalyst enantioselective regioselective hydrovinylation; alkenylarene preparation; C−C bond formation; alkenes; asymmetric catalysis; chirality; cobalt. The article conveys some information:

An efficient and practical protocol for the enantioselective cobalt-catalyzed hydrovinylation of vinylarenes with ethylene at low (1.2 bar) pressure was developed. As precatalysts, stable [L2CoCl2] complexes were employed that were activated in situ with Et2AlCl. A modular chiral TADDOL-derived phosphine-phosphite ligand was identified and that allowed the conversion of a broad spectrum of substrates including heterocyclic vinylarenes and vinylferrocene to smoothly afford the branched products with up to 99 % ee and virtually complete regioselectivity. Even polar functional groups such as OH, NH2, CN, and CO2R were tolerated. In the experiment, the researchers used many compounds, for example, (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: 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 aldehydesReference of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis