Month: October 2022

《Modified Amino Acid-Derived Phosphine-Imine Ligands for Palladium-Catalyzed Asymmetric Arylation of Cyclic N-Sulfonyl Imines》 was published in Advanced Synthesis & Catalysis in 2017. These research results belong to Zhou, Bo; Li, Kaizhi; Jiang, Chunhui; Lu, Yixin; Hayashi, Tamio. COA of Formula: C18H24NP The article mentions the following:

A series of chiral phosphine-imine ligands were synthesized starting with α-amino acids and examined for palladium-catalyzed asym. addition of arylboronic acids to cyclic N-sulfonyl imines. High catalytic activities (up to 99% yield) and high enantioselectivities (up to 98% ee) were achieved for cyclic N-sulfonyl aldimines and ketimines with five and six-membered ring structures. In the experiment, the researchers used many compounds, for example, (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2COA of Formula: C18H24NP)

(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.COA of Formula: C18H24NP 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

Formula: C50H56O14P2On November 14, 2003 ,《The development of a practical synthesis of the potent and selective somatostatin sst3 receptor antagonist [4-(3,4-difluoro-phenyl)-piperazine-1-yl]-{(4S,4aS,8aR)-2[(S)-3-(6-methoxy-pyridin-3-yl)-2-methyl-propyl]-decahydroisoquinoline-4-yl}-methanone (NVP-ACQ090)》 appeared in Tetrahedron: Asymmetry. The author of the article were Banziger, Markus; Cercus, Jacques; Hirt, Hans; Laumen, Kurt; Malan, Christophe; Spindler, Felix; Struber, Fritz; Troxler, Thomas. The article conveys some information:

The decahydroisoquinoline I (NVP-ACQ090) is a potent and selective antagonist at the somatostatin sst3 receptor. The original research synthesis of I comprises a main chain of nine linear steps and two side chains of three and steps, resp. This synthesis is highly convergent, but very complex and expensive, and involves several reagents that are not acceptable for a large scale synthesis. In chem. development, all the unacceptables could be replaced, and the overall efficiency of the synthesis was much improved. 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: 256390-47-3Formula: C50H56O14P2) 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. Formula: C50H56O14P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

SDS of cas: 960128-64-7On October 21, 2020 ,《Cationic NHC-Phosphine Iridium Complexes: Highly Active Catalysts for Base-Free Hydrogenation of Ketones》 was published in Chemistry – A European Journal. The article was written by Quan, Xu; Kerdphon, Sutthichat; Peters, Bram B. C.; Rujirawanich, Janjira; Krajangsri, Suppachai; Jongcharoenkamol, Jira; Andersson, Pher G.. The article contains the following contents:

Novel bidentate chiral N-heterocyclic carbene-phosphine iridium complexes [(cod)Ir(Ph2PC6H4CHR-1-NHC-3-R1)] (NHC = 2-imidazolylidene, 2-imidazolidinylidene, benzimidazolylidene; R = Me, Et, iPr; R1 = Me, iPr, CHMePh, PhCH2) have been synthesized and evaluated in the asym. hydrogenation of aryl ketones into chiral benzyl alcs. Reported catalytic systems require base additives and, if excluded, need elevated temperature or high pressure of hydrogen gas to achieve satisfactory reactivity. The developed catalysts showed extremely high reactivity and good enantioselectivity under base-free and mild conditions. In the presence of 1 mol % catalyst under 1 bar hydrogen pressure at room temperature, hydrogenation was complete in 30 min giving up to 96% ee. Again, this high reactivity was achieved in additive-free conditions. Mechanistic experiments demonstrated that balloon pressure of hydrogen was sufficient to form the activate species by reducing and eliminating the 1,5-cyclooctadiene ligand. The pre-activated catalyst was able to hydrogenate acetophenone with 89% conversion in 5 min. In the experiment, the researchers used (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas: 960128-64-7SDS of cas: 960128-64-7)

(R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas:960128-64-7) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.SDS of cas: 960128-64-7 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

Related Products of 960128-64-7On November 30, 2008 ,《Modular phosphine-aminophosphine ligands based on chiral 1,2,3,4-tetrahydro-1-naphthylamine backbone: a new class of practical ligands for enantioselective hydrogenations》 appeared in Advanced Synthesis & Catalysis. The author of the article were Qiu, Min; Hu, Xiang-Ping; Huang, Jia-Di; Wang, Dao-Yong; Deng, Jun; Yu, Sai-Bo; Duan, Zheng-Chao; Zheng, Zhuo. The article conveys some information:

New chiral phosphine-aminophosphine ligands [(R)-HW-Phos] were prepared from (R)-1,2,3,4-tetrahydro-1-naphthylamine through a two-step procedure, and successfully applied in the Rh-catalyzed asym. hydrogenation of various functionalized olefins such as α-enol ester phosphonates, α-enamido phosphonates, (Z)-β-(acylamino)acrylates and so on. Excellent enantioselectivities were achieved in the hydrogenation of most substrates tested, demonstrating the high potential of these newly developed phosphine-aminophosphine ligands in asym. catalysis. The present research also discloses that these newly developed phosphine-aminophosphine ligands are more efficient than that derived from (S)-1-phenylethylamine, suggesting that the increased rigidity conferred by a cyclohexyl fragment in these phosphine-aminophosphine ligands has a pos. effect in the asym. induction. In the part of experimental materials, we found many familiar compounds, such as (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas: 960128-64-7Related Products of 960128-64-7)

(R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas:960128-64-7) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Related Products of 960128-64-7 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

Qiu, Min; Hu, Xiang-Ping; Wang, Dao-Yong; Deng, Jun; Huang, Jia-Di; Yu, Sai-Bo; Duan, Zheng-Chao; Zheng, Zhuo published an article in Advanced Synthesis & Catalysis. The title of the article was 《Chiral 1,2,3,4-tetrahydro-1-naphthylamine-derived phosphine-phosphoramidite ligand (THNAPhos): application in highly enantioselective hydrogenations of functionalized C=C bonds》.Recommanded Product: 960128-64-7 The author mentioned the following in the article:

The authors recently reported a new chiral 1,2,3,4-tetrahydro-1-naphthylamine-derived phosphine-phosphoramidite ligand, (Rc,Ra)-THNAPhos, which is highly efficient in the Rh-catalyzed asym. hydrogenation of a broad range of α-enol ester phosphonates. To further demonstrate the utility of THNAPhos in asym. hydrogenation, its new application in the asym. hydrogenation of α-dehydroamino esters, enamides, itaconate, and α-enamido phosphonates was described. The Rh/(Rc,Ra)-THNAPhos complex is highly effective for the enantioselective hydrogenation of these kinds of olefins, affording the products in excellent enantioselectivity (normally >99% ee).(R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas: 960128-64-7Recommanded Product: 960128-64-7) was used in this study.

(R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas:960128-64-7) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Recommanded Product: 960128-64-7 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

The author of 《Tunable Bifunctional Phosphine-Squaramide Promoted Morita-Baylis-Hillman Reaction of N-Alkyl Isatins with Acrylates》 were Dong, Ze; Yan, Chao; Gao, Yongzhi; Dong, Chune; Qiu, Guofu; Zhou, Hai-Bing. And the article was published in Advanced Synthesis & Catalysis in 2015. Recommanded Product: (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine The author mentioned the following in the article:

A series of highly tunable bifunctional phosphine-squaramide H-bond donor organocatalysts I (R1 = i-Pr, Ph, t-Bu; R2 = 4-FC6H4, 3,5-(CF3)2C6H3, 3,5-(CF3)2C6H3CH2) has been synthesized from inexpensive and com. available β-amino alcs. in moderate yields. Catalyst I (R1 = t-Bu; R2 = 3,5-(CF3)2C6H3) can efficiently promote the asym. Morita-Baylis-Hillman (MBH) reaction of N-alkyl isatins with acrylate esters providing the chiral 3-substituted 3-hydroxy-2-oxindoles II (R3 = H, 4-Br, 5-F, etc.; R4 = Me, i-Pr, allyl, Bn, etc.; R5 = Me, Et, Bu, t-Bu) in good yields and enantioselectivities (up to 93 % yield and 95 % ee), in which the challenging substrate tert-Bu acrylate tert-Bu prop-2-enoate, provided the best ee value to date. This methodol. was applied successfully in the synthesis of chiral cyclic spiropyrrolizidineoxindole and γ-butyrolactone derivatives without enantioselectivity deterioration. The KIE experiments show that the electrophilic addition of N-Me isatin to the complex of acrylate ester and phophine-squaramide is the rate-determining step of the asym. MBH reaction. After reading the article, we found that the author used (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Recommanded Product: (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.Recommanded Product: (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

Application of 286454-86-2On March 17, 2017, Su, Hsin Y.; Taylor, Mark S. published an article in Journal of Organic Chemistry. The article was 《P-Stereogenic β-aminophosphines: preparation and applications in enantioselective organocatalysis》. The article mentions the following:

The synthesis of stereodefined β-aminophosphines ArPhPCH2CH(tBu)NH2 (1a,b, Ar = 2-MeOC6H4) having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alc.-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process. The products obtained are new building blocks for the synthesis of P-chiral ligands and organocatalysts. In a proof-of-concept application in organocatalysis, the diastereomeric P-chiral β-aminophosphine-based bifunctional thioureas displayed significantly different activities in the Morita-Baylis-Hillman reaction of Me acrylate with benzaldehyde derivatives In the experiment, the researchers used many compounds, for example, (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Application of 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.Application of 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

《Mechanistic insights into Cu-catalyzed enantioselective Friedel-Crafts reaction between indoles and 2-aryl-N-sulfonylaziridines》 was written by Wang, Ping; Zhao, Yang; Chapagain, Biplav; Yang, Yonggang; Liu, Wei; Wang, Yong. Product Details of 210169-54-3 And the article was included in Catalysis Science & Technology in 2020. The article conveys some information:

Computational studies were successfully carried out to provide mechanistic insights into LCu-catalyzed (L = (S)-Segphos ligand) Friedel-Crafts (F-C) reaction between indoles and 2-aryl-N-sulfonylaziridines. The proposed enantioselective mechanistic roles for the LCu-catalyzed F-C reaction were carefully considered: C-N bond cleavage through a three-membered ring transition state, C-C bond formation, oxidative addition, and reductive elimination. Through the energy decomposition anal. (EDA) on all possible transition states of the rate-determining step (RDS), the smaller ΔEdef(total) and the larger ΔEint were found in TS3R, resulting in the lowest activation energy (ΔE#). In other words, TS3R was the most kinetically favorable with the lowest activation barrier. Afterwards, the noncovalent interactions (C-H···π and π···π) and the steric effects were identified as playing a pivotal role in a favorable transition state for the C-C bond formation. In addition, the frontier MO (FMO) revealed that the smallest energy gap (5.2836 eV) between the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) was found in TS3R.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Product Details of 210169-54-3) was used in this study.

(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.Product Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Synthetic Route of C38H28O4P2In 2018 ,《Iridium-catalyzed Asymmetric Hydrogenation of Polycyclic Pyrrolo/Indolo[1,2-a]quinoxalines and Phenanthridines》 appeared in Advanced Synthesis & Catalysis. The author of the article were Hu, Shu-Bo; Zhai, Xiao-Yong; Shen, Hong-Qiang; Zhou, Yong-Gui. The article conveys some information:

Through in-situ protection of hydrogenation products with acetic anhydride to inhibit rearomatization and poisoning effect, an iridium-catalyzed enantioselective hydrogenation of polycyclic nitrogen-containing heteroaromatics – pyrrolo/indolo[1,2-a]quinoxalines and phenanthridines was successfully developed, providing a facile access to chiral dihydropyrrolo/indolo[1,2-a]quinoxalines and dihydrophenanthridines with up to 98% ee. The strategy featured broad substrate scope, easy operation and potential medicinal application.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Synthetic Route of C38H28O4P2) was used in this study.

(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 aldehydesSynthetic Route of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleIn 2016 ,《Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines》 appeared in Chemistry – A European Journal. The author of the article were Yan, Liang; Xu, Jing-Kun; Huang, Chao-Fan; He, Zeng-Yang; Xu, Ya-Nan; Tian, Shi-Kai. The article conveys some information:

A new strategy has been established for the kinetic resolution of racemic allylic alcs. through a palladium/sulfonyl-hydrazide-catalyzed asym. OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2, 4 mol % (S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcs. were smoothly resolved with selectivity factors of more than 400 through an asym. allylic alkylation of monosubstituted hydrazines under air at room temperature Importantly, this kinetic resolution process provided various allylic alcs. and allylic hydrazine derivatives with high enantiopurity. The results came from multiple reactions, including the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Safety 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 aldehydesSafety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis