Month: October 2022

The author of 《Enantioselective liquid-liquid extraction of DL-mandelic acid using chiral diphosphine ligands as extractants》 were Ma, Yu; Liu, Xiong; Zhou, Wenqi; Cao, Ting. And the article was published in Chirality in 2019. Related Products of 210169-54-3 The author mentioned the following in the article:

In order to expand the application range of chiral diphosphine ligands, (S)-BINAP, (S)-SEGPHOS, and (S)-MeO-BIPHEP were employed as extractants to recognize DL-mandelic acid. The results indicated that (S)-SEGPHOS-Cu exhibited considerable ability to recognize DL-mandelic acid with operational enantioselectivity (α) of 2.677. The process of extraction of DL-mandelic acid using (S)-SEGPHOS-Cu as extractant was systematically investigated. Performance factor (pf) was adopted to comprehensively evaluate the extraction After optimization by response surface methodol. (RSM), the optimal extraction condition is temperature of 5.5°C, (S)-SEGPHOS-Cu concentration of 3.0 mmol/L, and pH of 8.0. And the predicted and exptl. maximum values of pf were 0.26374 and 0.26839, resp. After reading the article, we found that the author used (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Related Products of 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.Related Products of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

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

The author of 《Synthesis of N-aryl β-amino acid derivatives via Cu(II)-catalyzed asymmetric 1,4-reduction in air》 were Li, Min; Xia, Hong-Feng; Yang, Li-Yao; Hong, Tao; Xie, Lin-Jie; Li, Shijun; Wu, Jing. And the article was published in RSC Advances in 2019. Electric Literature of C38H28O4P2 The author mentioned the following in the article:

In the presence of the inexpensive and stable stoichiometric reductant polymethylhydrosiloxane (PMHS) as well as certain amounts of appropriate alc. and base additives, the non-precious metal copper-catalyzed asym. 1,4-hydrosilylation of β-aryl or β-alkyl-substituted N-aryl β-enamino esters was well realized to afford a diverse range of N-aryl β-amino acid esters in high yields and excellent enantioselectivities (26 examples, 90-98% ee). This approach tolerated the handling of both catalyst and reactants in air without special precautions. The chiral products obtained were successfully converted to the corresponding enantiomerically enriched β-lactam and unprotected β-amino acid ester, which highlighted the synthetic utility of the developed catalytic procedure. In the experimental materials used by the author, we found (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Electric Literature 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.Electric Literature of C38H28O4P2

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

HPLC of Formula: 286454-86-2On October 12, 2017 ,《Dual-reagent organophosphine catalyzed asymmetric Mannich reactions of isocyanoacetates with N-Boc-aldimines》 was published in Tetrahedron. The article was written by Ji, Xiong; Cao, Wei-Guo; Zhao, Gang. The article contains the following contents:

A combination of an amino-acid derived chiral phosphine catalyst and Me acrylate has been employed to catalyze the direct Mannich reaction of α-aryl isocyanoacetate and N-Boc-aldimines efficiently. The loading of the catalyst could be as low as 0.5 mol% without compromise on the yield and enantioselectivity and the corresponding chiral adducts I (R = Me, Bn, t-Bu, i-Pr; Ar1 = Ph, 3-MeC6H4, 3-MeOC6H4, 4-BrC6H4, etc.; Ar2 = 3-MeC6H4, 3-MeOC6H4, 4-BFC6H4, etc.) were obtained in excellent yields (up to 98%) and good enantioselectivities (up to 95%). 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 2022,Xu, Qi; Zhang, Huan; Ge, Fang-Bei; Wang, Xiao-Mei; Zhang, Peng; Lu, Chuan-Jun; Liu, Ren-Rong published an article in Organic Letters. The title of the article was 《Cu(I)-Catalyzed Asymmetric Arylation of Pyrroles with Diaryliodonium Salts toward the Synthesis of N-N Atropisomers》.Product Details of 210169-54-3 The author mentioned the following in the article:

The copper(I) catalysis using a bis(phosphine) dioxide ligand could catalyze the desym. C-H arylation of prochiral bipyrroles was reported. More than 50 nitrogen-nitrogen atropisomers I [R1 = Ph, 3-ClC6H4, 2-naphthyl, etc.; R2 = Me, Et, Bn, etc.; R3 = Me, Et, i-Pr; R4 = H, Me; R1R4 = CH=CH-CH=CH; Ar = Ph, 4-MeC6H4, 3-ClC6H4, etc.] were achieved in good to excellent yields with excellent enantioselectivities (≤97% yield, ≤98% ee). The reaction proceeded under mild conditions with good functional group compatibility on arenes and diaryliodonium salts. Moreover, this principle enabled iterative arylation of the bipyrroles to enantioselectively arylate different positions during the catalysis of copper. 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: 210169-54-3Product 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) 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.Product Details of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Application of 286454-86-2On May 26, 2016, Chen, Peng; Su, Xiao; Zhou, Wei; Xiao, Yuanjing; Zhang, Junliang published an article in Tetrahedron. The article was 《Novel chiral sulfinamide phosphines: valuable precursors to chiral β-aminophosphines》. The article mentions the following:

Starting from com. available aldehyde and chiral tert-butanesulfinamide, chiral sulfinamide phosphines Ph2PCH2CH(R)NHS(:O)But (Xiao-Phos, R = alkyl, aryl, hetaryl) were synthesized via a two-step condensation-nucleophilic addition procedure. In most cases, nucleophilic addition of the N-tert-butanesulfinyl imine with [(diphenylphosphino)methyl]lithium (Ph2PCH2Li) showed high diastereoselectivity (d.r > 20:1) with BF3 as additives. Following removal of the chiral auxiliary, an important class of ligands i.e. chiral β-aminophosphines and its derivatives were obtained in high yields using this approach. The experimental part of the paper was very detailed, including the reaction process of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Application 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

In 2017,Wen, Lu; Yue, Zhenting; Zhang, Haiyan; Chong, Qinglei; Meng, Fanke published 《Cu-Catalyzed Enantioselective Boron Addition to N-Heteroaryl-Substituted Alkenes》.Organic Letters published the findings.Product Details of 210169-54-3 The information in the text is summarized as follows:

Catalytic enantioselective Cu-B(pin) (pin = pinacolato) addition to N-heteroaryl-substituted alkenes followed by protonation promoted by phosphine-Cu complexes is presented. The resulting alkylboron products that contain a N-heteroaryl moiety are afforded in up to 97% yield and 99:1 enantiomeric ratio. The highly versatile C-B(pin) bond can be converted to a range of useful functional groups, delivering a variety of enantiomerically enriched building blocks that are otherwise difficult to access. The utility of this method is further demonstrated by application to a fragment synthesis of biol. active mol. U-75302. Preliminary mechanistic studies revealed that the adjacent N atom of the heterocycles plays a unique role in high reactivity and enantioselectivity. In the experiment, the researchers used many compounds, for example, (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

In 2018,Qiu, Bo; Li, Xiao-Tong; Zhang, Jian-Yu; Zhan, Jun-Ling; Huang, Shuang-Ping; Xu, Tao published 《Catalytic Enantioselective Synthesis of 3,4-Polyfused Oxindoles with Quaternary All-Carbon Stereocenters: A Rh-Catalyzed C-C Activation Approach》.Organic Letters published the findings.Related Products of 210169-54-3 The information in the text is summarized as follows:

The first Rh-catalyzed enantioselective synthesis of a 3,4-polyfused oxindole ring system enabled by carboacylation of acrylic amides based on C-C activation is reported. This transformation provides a new entry to access 3,4-polyfused oxindoles bearing quaternary stereocenters. Tri- to pentacyclic 3,4-fused oxindoles were asym. generated in good yields (up to 95%) with good to excellent enantioselectivity (88%-97% ee). Application in the first total synthesis of xylanigripones A (I) was completed in 6 steps with a 14% overall yield. 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: 210169-54-3Related Products 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.Related Products of 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxoleIn 2020 ,《Ni-catalyzed enantioconvergent coupling of epoxides with alkenylboronic acids: construction of oxindoles bearing quaternary carbons》 was published in CCS Chemistry. The article was written by Wu, Liang; Yang, Guoqiang; Zhang, Wanbin. The article contains the following contents:

A nickel- nickel/bisphosphinecatalyzed stereoconvergent cross-coupling reaction of epoxides with alkenylboronic acids was developed . Racemic spiroepoxyoxindoles were converted to chiral homoallylic alcs. beared quaternary carbon stereogenic centers via a stereoablative enantioconvergent transformation. The subsequently fabricated oxindoles-carrying quaternary carbon products were obtained in good yields and enantioselectivity. A wide range of substrates and alkenylboronic acids was tolerated under the catalytic system. This reaction provided a rare example of a nickel catalyzed enantioselective cross-coupling reaction of tertiary alkyl electrophiles and an enantioconvergent transformation of racemic epoxides, beneficial as a low-cost, sustainable, and efficient catalyst in the preparation of chiral oxindole-containing natural and pharmaceutical compounds In the experiment, the researchers used many compounds, for example, (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: 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 aldehydesQuality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis