Day: October 17, 2022

《Catalytic enantioselective alkylation of 2-alkoxy-tetrahydrofurans》 was published in Organic Chemistry Frontiers in 2020. These research results belong to Liu, Xuan; Sun, Shaofa; Wang, Gang; Bai, Zhushuang; Pang, Jingxiang; Liu, Lei. Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article mentions the following:

Catalytic asym. addition to non-resonance-stabilized oxocarbenium ions has remained a formidable challenge. Herein, a nickel(II)-catalyzed asym. alkylation of non-resonance-stabilized, five-membered oxocarbenium ions generated in situ from 2-alkoxy tetrahydrofurans I (R = Et, n-Pn, Bn, t-Bu) with a broad range of carboxylic acid derivatives II (X = O, S; R1 = 4-fluorophenyl, naphthalen-1-yl, pent-1-en-1-yl, etc.) was disclosed. The reaction exhibits high efficiency, excellent enantioselectivity, and good functional group tolerance, and can be conducted on a large scale. Aside from five-membered oxocarbenium ions, six-membered 2-(pentyloxy)oxane and acyclic aliphatic species such as 1,1-dimethoxyhexane, Me 5,5-dimethoxyvalerate were also well tolerated with excellent enantiocontrol, thus providing a practical and robust method to access enantiopure α-alkyl substituted saturated ethers e.g., III. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Quality Control 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: 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.Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Reversal of diastereoselectivity in palladium-arene interaction directed hydrogenative desymmetrization of 1,3-diketones》 was written by Yu, Chang-Bin; Wang, Heng-Ding; Song, Bo; Shen, Hong-Qiang; Fan, Hong-Jun; Zhou, Yong-Gui. Synthetic Route of C38H28O4P2 And the article was included in Science China: Chemistry in 2020. The article conveys some information:

Herein, an unprecedented trans reductive products were observed in palladium-catalyzed hydrogenative desymmetrization of cyclic and acyclic 1,3-diketones, providing the chiral trans β-hydroxy ketones with two adjacent stereocenters including one α-tertiary or quaternary stereocenter with high enantioselectivity and diastereoselectivity. Mechanistic studies and DFT calculations suggested that the rarely observed diastereoselectivity reversal is ascribed to the charge-charge interaction between the palladium and aromatic ring of the substrate, which could not only result in the reversal of the diastereoselectivity, but also improve the reactivity. The experimental process involved 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) 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

Ebisu, Yasuhiro; Kawamura, Kenjiro; Hayashi, Masahiko published an article in Tetrahedron: Asymmetry. The title of the article was 《Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones using a novel N,N,P-Cu(II) complex》.Application of 286454-86-2 The author mentioned the following in the article:

Enantioselective copper-catalyzed 1,4-additions of dialkylzincs R2Zn (R = Et, Me) to enones I [X = (CH2)n, n = 0-2] and II (R1 = H, R2 = H, Me; R1 = MeO, NO2, F, R2 = H) were carried out in the presence of 1 mol % of Cu(OTf)2 and 2.5 mol % of an N,N,P-ligand possessing a tert-Bu group at the adjacent position of the nitrogen of pyridine to afford the corresponding 1,4-adducts III and IV, resp., in up to 98% ee. The results came from multiple reactions, including the reaction of (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

《Water-Promoted Palladium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Alkoxysilanes》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to Tan, Yun; Yao, Yongqi; Yang, Wen; Lin, Qifu; Huang, Guobao; Tan, Minxiong; Chen, Shuqi; Chen, Donghan; Yang, Dingqiao. Application In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article mentions the following:

Water-promoted palladium-catalyzed asym. ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of alkoxysilanes was developed in a one-pot fashion, yielding cis-1,2-dihydronaphthalen-1-ols I [R1 = CH=CH2, Ph, 1-naphthyl, etc.; R2 = H, OMe; R3 = H, Me, Br, etc.; R4 = H, Me, F, etc.; R5 = H, OMe] in favorable yields (up to 98%) with gratifying enantioselectivities (up to 98% ee) under mild conditions. Furthermore, the cis-1,2-configuration of product was established by X-ray diffraction anal., and a possible mechanism for the present catalytic ring-opening reaction was also proposed. In the experiment, the researchers used many compounds, for example, (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Application In Synthesis 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) 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.Application In Synthesis of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2022,Chen, Wenchang; Yi, Xiaofen; Qu, Hongmin; Chen, Yu; Tang, Pei; Chen, Fener published an article in Chinese Chemical Letters. The title of the article was 《Concise syntheses of 13-methylprotoberberine and 13-methyltetrahydroprotoberberine alkaloids》.Product Details of 210169-54-3 The author mentioned the following in the article:

The concise syntheses of eight 13-methylprotoberberine (13-MePB) and eight enantioenriched 13-methyltetrahydroprotoberberine (13-MeTHPB) alkaloids have been achieved in a tactically modular fashion. This synthetic work features a one-pot metal-free Pictet-Spengler/Friedel-Crafts hydroxyalkylation/dehydration/oxidation sequence and a following highly enantioselective Ir-catalyzed hydrogenation. Given such brevity and modularity, our developed synthetic route would be greatly beneficial to the efficient syntheses of existing natural products and new fully synthetic variants of 13-MePB and 13-MeTHPB family. 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: 210169-54-3Product Details of 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 aldehydesProduct Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《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