Category: chiral-phosphine-ligands

Wang, Cong-Shuai; Wei, Liang; Fu, Cong; Wang, Xin-Heng; Wang, Chun-Jiang published their research in Organic Letters in 2021. The article was titled 《Asymmetric Synthesis of Axially Chiral Naphthyl-C3-indoles via a Palladium-Catalyzed Cacchi Reaction》.Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article contains the following contents:

Atropoisomeric biaryl motifs are widely found in natural products and bioactive compounds as well as chiral catalysts and ligands. Various efficient approaches have been disclosed for the construction of chiral six-six biaryl skeletons. In contrast, the enantioselective synthesis of axially chiral arylindoles through the strategy of de novo construction, other than the asym. functionalization of indoles, remain a challenging task. Herein authors report an efficient Pd(0)/(S)-Segphos-catalyzed atroposelective Cacchi reaction of 2-alkynylanilines with sterically congested naphthyl halides, which afforded an array of naphthyl-C3-indoles in high yields with good to excellent atroposelectivities. The addition of water and the modulation of the manipulation procedure by premixing the palladium complex and the naphthyl halide were the keys to success. The conformational stability of the obtained axially chiral naphthyl-C3-indole containing a synthetically more-valuable free NH moiety is revealed through kinetic experiments The experimental process involved 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) 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

The author of 《Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives》 were Wang, Gang; Xin, Xiaodong; Wang, Zehua; Lu, Gang; Ma, Yudao; Liu, Lei. And the article was published in Nature Communications in 2019. Computed Properties of C38H28O4P2 The author mentioned the following in the article:

A formal catalytic enantioselective cross-dehydrogenative coupling of saturated ethers with diverse carboxylic acid derivatives involving an initial oxidative acetal formation, followed by nickel(II)-catalyzed asym. alkylation. The one-pot, general and modular method exhibited wide compatibility of a broad range of saturated ethers not only including prevalent THF and tetrahydropyran but also including medium- and large-sized cyclic moieties and acyclic ones with excellent enantioselectivity and functional group tolerance. The application in the rapid preparation of biol. active mols. that are difficult to access with existing methods was also demonstrated. 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: 210169-54-3Computed Properties 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: 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.Computed Properties of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2019,Organic Letters included an article by Quintard, Adrien; Rodriguez, Jean. Category: chiral-phosphine-ligands. The article was titled 《Enantioselective Ir-Catalyzed Bidirectional Reductive Coupling》. The information in the text is summarized as follows:

In the presence of a chiral iridium complex, com. available 3-chloro-2-chloromethyl-1-propene (1) was selectively activated for various reductive couplings. Depending on the reaction conditions it allows a selective mono- or bidirectional condensation with one or two external aldehydes with excellent enantiocontrol (>90% ee). This approach occurring simply under mild conditions and avoiding premetalated reagents constructs rapidly chiral homoallylic alcs., key precursors of important mol. fragments such as furans, pyrans, ketodiols, or 1,3,5-polyols. The results came from multiple reactions, including the reaction of (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) 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.Category: chiral-phosphine-ligands

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

SDS of cas: 256390-47-3On November 3, 2017 ,《Palladium-Catalyzed Asymmetric Allylic Alkylation of Alkyl-Substituted Allyl Reagents with Acyclic Amides》 appeared in Organic Letters. The author of the article were Jiang, Yang-Jie; Zhang, Gao-Peng; Huang, Jian-Qiang; Chen, Di; Ding, Chang-Hua; Hou, Xue-Long. The article conveys some information:

A wide range of alkyl-substituted allyl reagents, as well as nonstabilized carbon nucleophiles, was successfully used for the first time in the palladium-catalyzed asym. allylic alkylation reaction, affording the corresponding allylic alkylated products in high yields with high enantioselectivities. The usefulness of the protocol has been demonstrated by the enantioselective synthesis of an important chiral building block and enantiomer of Dubiusamine A. The experimental part of the paper was very detailed, including the reaction process of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3SDS of cas: 256390-47-3)

(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. SDS of cas: 256390-47-3 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

Related Products of 256390-47-3On March 31, 2011, Khan, Hasan A.; Kou, Kevin G. M.; Dong, Vy M. published an article in Chemical Science. The article was 《Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of benzoxazecinones》. The article mentions the following:

A method for a nitrogen-directed ketone hydroacylation is reported to furnish eight-membered nitrogen-containing lactone (benzoxazecinone) derivatives in high yield and high enantiomeric excess. In a model study, a comparison was made between nitrogen, oxygen and sulfur directing groups and it was found that nitrogen promoted faster hydroacylation. By this catalytic transformation the synthesis of the target compounds (i.e., nitrogen heterocyclic compounds, benzoxazepinone derivatives and benzoxazecinone derivatives) was achieved and it was discovered that, moreover, an amine-directing group completely suppressed a competitive decarbonylation reaction. The experimental part of the paper was very detailed, including the reaction process of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Related Products of 256390-47-3)

(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. Related Products of 256390-47-3 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

The author of 《Highly Enantioselective Rhodium-Catalyzed Cross-Addition of Silylacetylenes to Cyclohexadienone-Tethered Internal Alkynes》 were Duan, Chang-Lin; Tan, Yun-Xuan; Zhang, Jun-Li; Yang, Shiping; Dong, Han-Qing; Tian, Ping; Lin, Guo-Qiang. And the article was published in Organic Letters in 2019. Computed Properties of C38H28O4P2 The author mentioned the following in the article:

The first highly enantioselective rhodium-catalyzed cross-addition of silylacetylenes to cyclohexadienone-tethered internal alkynes has been achieved via a tandem process: regioselective alkynylation of the internal alkynes and subsequent intramol. conjugate addition to the cyclohexadienones, affording the cis-hydrobenzofuran frameworks with good yields (up to 88% yield) and excellent enantioselectivities (90%-96% ee). This mild reaction showed perfect atom economy and broad functional group tolerance. Furthermore, a gram-scale experiment and diverse further conversions of the cyclization products were also presented. 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: 210169-54-3Computed Properties 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.Computed Properties of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2017,Kim, Seung Wook; Lee, Wonchul; Krische, Michael J. published 《Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer》.Organic Letters published the findings.Electric Literature of C38H28O4P2 The information in the text is summarized as follows:

Glycidols prepared via Sharpless asym. epoxidation participate in asym. redox-neutral carbonyl allylation with good levels of catalyst-directed diastereoselectivity. Equally stereoselective allylations may be performed from the aldehyde oxidation level using 2-propanol as the terminal reductant. An epoxide ring-opening reaction using AlMe3-n-BuLi is used to prepare the propionate-based stereotetrad spanning C17-C23 of dictyostatin, illustrating how this method may be applied to polyketide construction. In the experiment, the researchers used many compounds, for example, (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) 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 aldehydesElectric Literature of C38H28O4P2

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis