Chiral phosphine ligands

Zhao, Zhi; Yang, Xing-Xing; Ran, Guang-Yao; Ouyang, Qin; Du, Wei; Chen, Ying-Chun published an article in 2021. The article was titled 《Ligand-Controlled Regiodivergent Asymmetric [5 + 2] and [3 + 2] Annulations of Vinyl Indoloxazolidones Catalyzed by Palladium》, and you may find the article in Organic Letters.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The information in the text is summarized as follows:

Here, authors present palladium-catalyzed regiodivergent asym. annulations of vinyl indoloxazolidones, which can act as 1,5-carbodipoles or 1,3-carbodipoles by tuning the chiral ligands and conditions, in the assemblies with sulfamate-derived cyclic imines and even activated alkenes. A diversity of polycyclic products are generally constructed with high regio- and enantioselectivity. 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: 210169-54-3Safety 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) 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.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Direct catalytic asymmetric and anti-selective vinylogous addition of butenolides to chromones》 was published in Chemical Science in 2020. These research results belong to Cui, Jin; Kumagai, Naoya; Watanabe, Takumi; Shibasaki, Masakatsu. COA of Formula: C50H56O14P2 The article mentions the following:

An anti-selective catalytic asym. Michael-type vinylogous addition of β,γ-butenolides to chromones was developed. The catalyst system developed herein is characterized by tuning of the steric and electronic effects using a proper Biphep-type chiral ligand to invert the diastereoselection, and improvement of the catalyst turnover by a coordinative phenolic additive. The catalytic protocol renders potentially biol. active natural product analogs accessible in good yield with moderate diastereoselectivity and high enantiomeric purity, mostly greater than 99% ee. 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: 256390-47-3COA of Formula: 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. 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. COA of Formula: C50H56O14P2

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

In 2019,Chemical Science included an article by Yang, Tao; Guo, Xiaochong; Yin, Qin; Zhang, Xumu. Application of 210169-54-3. The article was titled 《Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines》. The information in the text is summarized as follows:

An Ir-catalyzed intramol. asym. reductive amination (ARA) of bridged biaryl derivatives has been described. Using this unprecedented approach, synthetically useful dibenz[c,e]azepines containing both central and axial chiralities are obtained with excellent enantiocontrol (up to 97% ee). This methodol. represents a rare example of enantioselective chemocatalytic synthesis of chiral dibenz[c,e]azepines featuring a broad substrate scope, and their synthetic utilities are exhibited by derivatizing the products into a chiral amino acid derivative and chiral phosphoramidite ligands, which display excellent enantiocontrol in Rh-catalyzed asym. hydrogenation of α-dehydroamino acid derivatives Remarkably, this method is also applicable to enantioselectively synthesize an allocolchicine analog. In addition to this study using (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, there are many other studies that have used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Application of 210169-54-3) was used in this study.

(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 of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《A D-Camphor-Based Schiff Base as a Highly Efficient N,P Ligand for Enantioselective Palladium-Catalyzed Allylic Substitutions》 was published in ChemCatChem in 2016. These research results belong to Liu, Qiao-Ling; Chen, Weifeng; Jiang, Qun-Ying; Bai, Xing-Feng; Li, Zhifang; Xu, Zheng; Xu, Li-Wen. Product Details of 960128-64-7 The article mentions the following:

New Schiff bases derived from chiral D-camphor were determined to be effective phosphine ligands for the asym. palladium-catalyzed allylic alkylation of activated methylene compounds, the allylic etherification of alcs., and the allylic amination of primary amines or secondary amines, in which the corresponding products with various functional groups were achieved in good yields with excellent enantioselectivities (up to >99 % ee). Remarkably, the palladium catalyst derived from Schiff base L2 afforded the highest level of enantioselectivity reported to date for allylic substitution reactions, including allylic etherification and allylic amination, which revealed the privileged role of D-camphor-derived Schiff bases in palladium-catalyzed allylic substitution reactions. After reading the article, we found that the author used (R)-8-(Diphenylphosphino)-1,2,3,4-tetrahydronaphthalen-1-amine(cas: 960128-64-7Product Details 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.Product Details 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

Synthetic Route of C50H56O14P2On October 7, 2016 ,《Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones》 was published in Organic Letters. The article was written by Meng, Ling; Jin, Ming Yu; Wang, Jun. The article contains the following contents:

A highly efficient asym. synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using [Rh(COD)Cl]2/(R)-3,4,5-MeO-BIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asym. synthesis paves the way for further pharmaceutical studies.(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Synthetic Route of 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. Synthetic Route of C50H56O14P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Wang, Zhen; Wang, Dong-Chao; Xie, Ming-Sheng; Qu, Gui-Rong; Guo, Hai-Ming published an article in Organic Letters. The title of the article was 《Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans》.Reference of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine] The author mentioned the following in the article:

A straight synthetic approach to fused polycyclic tropane scaffold formation through an asym. dearomatization cycloaddition process of 2-nitrobenzofurans with cyclic azomethine ylides was successfully developed. In the presence of a chiral copper complex, derived from Cu(OAc)2 and a diphosphine ligand, a series of fused polycyclic tropane derivatives (e.g. I)were obtained in high yields (75-91%) with excellent enantioselectivities (90-98%). The utility of this method was showcased by the facile transformation of product. In the part of experimental materials, we found many familiar compounds, such as (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Reference of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine])

(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. Reference of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine]

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2019,Organic Letters included an article by Zhao, Xiang; Zhang, Feng; Liu, Kai; Zhang, Xumu; Lv, Hui. Recommanded Product: 210169-54-3. The article was titled 《Nickel-Catalyzed Chemoselective Asymmetric Hydrogenation of α,β-Unsaturated Ketoimines: An Efficient Approach to Chiral Allylic Amines》. The information in the text is summarized as follows:

An efficient synthetic route to chiral allylic amines R1R2C:CHCHR3NHR4 (R1 = Ph, 2-naphthyl, 2-furyl, etc; R2 = H, Me; R3 = Ph, 3-FC6H4, 4-MeOC6H4, etc.; R4 = Ms, SO2NMe2, Ts) has been developed by nickel/(S,S)-Ph-BPE complex catalyzed chemoselective asym. hydrogenation of α,β-unsaturated ketoimines. Varieties of α,β-unsaturated ketoimines have been well tolerated in this transformation to give chiral allylic amines with high yields and excellent ee values (up to 99% yield, up to 99% ee). A gram-scale reaction with 0.2 mol % catalyst loading has also been achieved. The results came from multiple reactions, including the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Recommanded Product: 210169-54-3)

(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.Recommanded Product: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

SDS of cas: 210169-54-3In 2019 ,《Catalytic Enantioselective Synthesis of Azepine-Fused Planar-Chiral Ferrocenes by Pt-Catalyzed Cycloisomerization》 appeared in Organometallics. The author of the article were Ito, Mamoru; Okamura, Moeka; Kanyiva, Kyalo Stephen; Shibata, Takanori. The article conveys some information:

Enantioselective synthesis of azepine-fused planar-chiral ferrocenes was achieved by the chiral cationic Pt-catalyzed intramol. cycloisomerization of N-propargyl-2-ferrocenylanilines. A mechanistic study using an N-allenyl analog indicated that the reaction proceeded selectively in a 7-exo-dig manner along with isomerization of the exo-olefin moiety. A methanesulfonylamino tether was crucial for selective cycloisomerization. This is the 1st example of the enantioselective synthesis of heteropin-fused planar-chiral ferrocenes. 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: 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.SDS of cas: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Ito, Masato; Osaku, Akihide; Kobayashi, Chika; Shiibashi, Akira; Ikariya, Takao published an article on January 26 ,2009. The article was titled 《A Convenient Method for the Synthesis of Protic 2-(Tertiary phosphino)-1-amines and Their Cp*RuCl Complexes》, and you may find the article in Organometallics.COA of Formula: C18H24NP The information in the text is summarized as follows:

A variety of protic 2-(tertiary phosphino)-1-amines (R2PCH2CHR’NHR”, P-NH) were prepared from 2-oxazolidinones and secondary phosphines using a newly developed acid-promoted decarboxylative C-P bond formation reaction. Treatment of the resulting chiral P-NH compounds with Cp*RuCl(isoprene) in CH2Cl2 smoothly furnished chiral Cp*RuCl(P-NH) complexes with a typical three-legged piano-stool structure, which prove to be excellent catalyst precursors for asym. reactions, including the isomerization of allylic alcs. and hydrogenation of imides. After reading the article, we found that the author used (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