Category: 503538-69-0

Yang, Zhiping published the artcileEnantioselective Palladium-Catalyzed Hydrophosphinylation of Allenes with Phosphine Oxides: Access to Chiral Allylic Phosphine Oxides, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2021), 60(52), 27288-27292, database is CAplus and MEDLINE.

A Pd-catalyzed hydrophosphinylation of alkyl and aryl-oxyallenes with phosphine oxides has been developed for the efficient and rapid construction of a family of chiral allylic phosphine oxides with a diverse range of functional groups. This methodol. was further applied in the facile construction of chiral 2H-chromene and later stage functionalization of cholesterol.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C9H9ClN2, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Praetorius, Jeremy M. published the artcileBenzimidazoles as Ligands in the Ruthenium-Catalyzed Enantioselective Bifunctional Hydrogenation of Ketones, Category: dioxole, the publication is Organometallics (2010), 29(3), 554-561, database is CAplus.

A series of Cl₂Ru(diphosphane)L₂ (II) complexes in which L = N1-alkylated benzimidazoles, bonding to the metal through nitrogen, have been synthesized and characterized. In the case of 1-methylbenzimidazole, the resulting complexes exist as statistical mixtures of all possible conformational isomers. When the size of the substituent on the benzimidazole was increased to trityl, complexes could be prepared that exist as a single diastereomer. All complexes possessing benzimidazole ligands bound to the ruthenium center are active for the mild and chemoselective hydrogenation of ketones in the presence of alkenes. Catalysts that exist as a single diastereomer, prepared with enantiomerically pure diphosphanes, catalyze the hydrogenation of prochiral ketones with moderate levels of enantioselectivity that are significantly improved relative to catalysts existing in several conformations.

Organometallics published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Category: dioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Yang, Qingjing published the artcileKinetic Resolution and Dynamic Kinetic Resolution of Chromene by Rhodium-Catalyzed Asymmetric Hydroarylation, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2019), 58(16), 5343-5347, database is CAplus and MEDLINE.

A highly efficient kinetic resolution and dynamic kinetic resolution of chromene was reported for the first time and they proceeded by a rhodium-catalyzed asym. hydroarylation pathway. This new approach offered versatile access to various chiral 2,3-diaryl-chromanes containing vicinal stereogenic centers, as well as the recovered chiral flavenes, in high yields with excellent ee values (s factor up to 532). Particularly noteworthy was that this strategy could be further extended to the establishment of a dynamic version of the kinetic resolution of chromene acetals and allowed complete access to chiral isoflavanes and α-aryl hydrocoumarins.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C39H35N5O8, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Wang, Cong-Shuai published the artcileAsymmetric Synthesis of Axially Chiral Naphthyl-C3-indoles via a Palladium-Catalyzed Cacchi Reaction, Formula: C38H24F4O4P2, the publication is Organic Letters (2021), 23(19), 7401-7406, database is CAplus and MEDLINE.

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

Organic Letters published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C6H5F4NO3S, Formula: C38H24F4O4P2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Liao, Xuebin published the artcileEnantioselective α-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Journal of the American Chemical Society (2008), 130(1), 195-200, database is CAplus and MEDLINE.

The asym. α-arylation of ketones with aryl triflates is described, and the use of this electrophile with nickel and palladium catalysts containing a segphos derivative increases substantially the scope of highly enantioselective arylations of ketone enolates. The combination of aryl triflates as reactant, difluorphos as ligand, palladium catalysts for reactions of electron-neutral or electron-rich aryl triflates, and nickel catalysts for reactions of electron-poor aryl triflates led to a series of α-arylations of tetralone, indanone, cyclopentanone, and cyclohexanone derivatives Enantioselectivities ranged from 70% to 98% with 10 examples over 90%. Systematic studies on these α-arylations have revealed a number of factors that affect enantioselectivity. Ligands containing biaryl backbones with smaller dihedral angles generate catalysts that react with higher enantioselectivity than related ligands with larger dihedral angles. In addition, faster rates for reactions of aryl triflates vs. those for reactions of aryl bromides allow the α-arylations of aryl triflates to be conducted at lower temperatures, and this lower temperature improves enantioselectivity. Finally, studies that compare the enantioselectivities of catalytic reactions to those of stoichiometric reactions of isolated [(segphos)Pd(Ar)(Br)], [(segphos)Pd(Ar)(I)], and [(segphos)Ni(C₆H₄CN-4)Br] suggest that catalyst decomposition affects enantioselectivity.

Journal of the American Chemical Society published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

He, Zhi-Tao published the artcileEfficient access to bicyclo[4.3.0]nonanes: copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-tethered allenes, Formula: C38H24F4O4P2, the publication is Angewandte Chemie, International Edition (2015), 54(49), 14815-14818, database is CAplus and MEDLINE.

The creation of three consecutive chiral carbon centers in one step is achieved using Cu-catalyzed asym. silylative cyclization of cyclohexadienone-tethered allenes I (1a–x), in reaction with PhMe₂SiBpin (2), catalyzed by CuCl/L or CuCl/L₂ (L = BINOL phosphoramidite; L₂ = BIPHEP, Segphos, Difluorphos, P-Phos, etc.), giving bicyclic enones II (3a–x; X = O, NBoc, CH₂; R = Me, Cy, PhCH₂, BocNHCH₂CH₂, alkoxy, CH₂:CH, Ph, MeO₂CCH₂, haloalkyl, aryl); the products 3 were obtained with >90% ee, either as pure diastereomer or with (15-20):1 ratio of (3S,3aR,7aR):(3S,3aS,7aS) diastereomers. The requisite allenyl-tethered cyclohexadienones 1a–r were prepared by oxidative etherification of phenols 4-RC₆H₄OH with propargyl alc. CHCCH₂OH to give cyclohexadienone propargyl ethers HCCCH₂O(R)(CH:CH)₂CO with subsequent CuBr-catalyzed formaldehyde addition Through regioselective β-silylation of the allene and subsequent enantioselective 1,4-addition to cyclohexadienone, this tandem reaction could afford cis-hydrobenzofuran, cis-hydroindole, and cis-hydroindene frameworks with excellent yields (80-98%) and enantioselectivities (94-98 % ee) bearing vinylsilane and enone substructures. Meanwhile, this mild transformation is generally compatible with a wide range of functional groups, which allows further conversion of the bicyclic products to bridged and tricyclic ring structures.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Formula: C38H24F4O4P2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Takahashi, Masashi published the artcileAtropisomeric lactam chemistry: catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors, HPLC of Formula: 503538-69-0, the publication is Tetrahedron (2010), 66(1), 288-296, database is CAplus.

In the presence of an (R)-SEGPHOS and Pd(OAc)₂ catalyst system, the intramol. N-arylation of ortho-tert-butyl-NH-anilides possessing an iodophenyl group, e.g., I, proceeded in a highly enantioselective manner (89-98% ee) to give optically active atropisomeric lactams, e.g., II, having an N-C chiral axis. MPLC purification of the enantio-enriched lactam products using an achiral silica gel column led to a further increase in the enantiomeric purity (>99% ee). The reaction of the lithium enolate prepared from the optically active atropisomeric lactam with various alkyl halides gave α-substituted and α,α-disubstituted lactam products with high diastereoselectivity. α-Alkylated lactam derivatives were efficiently converted to key intermediates for the synthesis of a norepinephrine transporter inhibitor.

Tetrahedron published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C6H12N2O, HPLC of Formula: 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Tang, Weijun published the artcileHighly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst, HPLC of Formula: 503538-69-0, the publication is Organic & Biomolecular Chemistry (2010), 8(15), 3464-3471, database is CAplus and MEDLINE.

The combination of the readily available chiral bisphosphine ligand Difluorphos with [Ir(COD)Cl]₂ in THF resulted in a highly efficient catalyst system for asym. hydrogenation of quinolines at quite low catalyst loadings (0.05-0.002 mol%), affording the corresponding products with high enantioselectivities (up to 96%), excellent catalytic activities (TOF up to 3510 h^-1) and productivities (TON up to 43000). The same catalyst was also successfully applied to the asym. hydrogenation of trisubstituted pyridines with nearly quant. yields and up to 98% ee. In these two reactions, the addition of I₂ additive is indispensable; but the amount of I₂ has a different effect on catalytic performance.

Organic & Biomolecular Chemistry published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C2H4ClNO, HPLC of Formula: 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Alame, Mohamad published the artcileExtensive re-investigations of pressure effects in rhodium-catalyzed asymmetric hydrogenations, COA of Formula: C38H24F4O4P2, the publication is Advanced Synthesis & Catalysis (2008), 350(6), 898-908, database is CAplus.

The catalytic hydrogenation of three prochiral substrates Me Z-α-acetamidocinnamate (MAC), Me 2-acetamidoacrylate (M-Acrylate) and Et 4-methyl-3-acetamido-2-propanoate (E-EMAP) with rhodium precursors complexed with chiral diphosphines is reported at 1-30 bar hydrogen pressure. A library of 56 chiral diphosphines, including 23 BINAP derivatives, 7 JOSIPHOS, 5 BIPHEP, 3 DUPHOS derivatives, and 18 other ligands, was used. While it was generally accepted that high hydrogen pressure would result in lower ees, it is now demonstrated on a statistical basis that an equivalent distribution between beneficial and detrimental pressure effects on ee prevails and that the hydrogen pressure effect on enantioselectivity is not an isolated phenomenon since more than 33% of the reaction systems studied are strongly affected. In some case, the enantioselectivity can be improved up to 97% just by applying a higher hydrogen pressure. Extension of these conclusions to other non-chiral reagents is proposed.

Advanced Synthesis & Catalysis published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, COA of Formula: C38H24F4O4P2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Menard, Frederic published the artcileLigand-Controlled Selectivity in the Desymmetrization of meso Cyclopenten-1,4-diols via Rhodium(I)-Catalyzed Addition of Arylboronic Acids, SDS of cas: 503538-69-0, the publication is Journal of Organic Chemistry (2010), 75(12), 4056-4068, database is CAplus and MEDLINE.

A highly enantioselective desymmetrization of meso cyclopent-2-ene-1,4-diethyl dicarbonates has been developed using a Rh-catalyzed asym. allylic substitution. Depending on the type of ligand used, each of two regioisomeric products can be obtained in good yield and excellent enantioselectivity. Under rhodium(I) catalysis, bisphosphine P-Phos ligands form trans-1,2-arylcyclopentenols as the major product, whereas Segphos ligands lead predominantly to trans-1,4-arylcyclopentenols.

Journal of Organic Chemistry published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, SDS of cas: 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem