Category: 126613-06-7

Yang, Lei published the artcileChiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C-H Arylation, Safety of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Angewandte Chemie, International Edition (2018), 57(5), 1394-1398, database is CAplus and MEDLINE.

Previous enantioselective Pd⁰-catalyzed C-H activation reactions proceeding via the concerted metalation-deprotonation mechanism employed either a chiral ancillary ligand, a chiral base, or a bimol. mixture thereof. This study describes the development of new chiral bifunctional ligands based on a binaphthyl scaffold which incorporates both a phosphine and a carboxylic acid moiety. The optimal ligand provided high yields and enantioselectivities for a desymmetrizing C(sp²)-H arylation leading to 5,6-dihydrophenanthridines, whereas the corresponding monofunctional ligands showed low enantioselectivities. The bifunctional system proved applicable to a range of substituted dihydrophenanthridines, and allowed the parallel kinetic resolution of racemic substrates.

Angewandte Chemie, International Edition published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C7H6O3, Safety of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Yanagisawa, Akira published the artcileCatalytic asymmetric aldol reaction of trimethoxysilyl enol ethers using 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl·AgF complex, Quality Control of 126613-06-7, the publication is Bulletin of the Chemical Society of Japan (2001), 74(8), 1477-1484, database is CAplus.

Catalytic asym. Mukaiyama-type aldol reaction using MeO₃Si enol ethers was achieved using 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl (p-Tol-BINAP)·AgF complex as a catalyst. The chiral Ag(I) catalyst was easily generated by mixing p-Tol-BINAP and AgF in MeOH at room temperature High syn- and enantioselectivities were obtained from both the E- and Z-silyl enol ethers. Use of a 1:1 mixture of MeOH and acetone as a solvent in the reaction of cyclohexanone-derived MeO₃Si enol ethers resulted in higher enantioselectivity.

Bulletin of the Chemical Society of Japan published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H32O2, Quality Control of 126613-06-7.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Rafter, Eoin published the artcileSynthesis of P-stereogenic BINAP bissulfide analogues, Application of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Tetrahedron: Asymmetry (2011), 22(16-17), 1680-1686, database is CAplus.

BINAP disulfide analogs (1R)-C₂₀H₁₂-2-P(S)Ph₂-2′-P(S)R¹R² (11–15, R¹, R²: Me, Ph; 2-MeOC₆H₄, Ph; 2-MeC₆H₄, Ph; 2-MeOC₆H₄, 2-MeOC₆H₄; 2-MeC₆H₄, 2-MeC₆H₄), containing stereogenic phosphorus center, were prepared by phosphination of 2,2′-BINOL ditriflate with HPPh₂, HPR¹R³ and phosphine oxides with subsequent sulfuration. The synthesis of these ligands was achieved by step-wise palladium and nickel-catalyzed coupling reactions of the precursor binaphthyl triflate with secondary phosphines and phosphine oxides, resp. C₂-Unsym. BINAP bissulfide analogs with the same aryl substituents were also synthesized for the sake of comparison. Preliminary studies of the reduction of these sulfides to the free phosphines are also described.

Tetrahedron: Asymmetry published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, Application of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Takahashi, Motohiro published the artcileLarge Scale Synthesis of Chiral (3Z,5Z)-2,7-Dihydro-1H-azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids, Category: esters-buliding-blocks, the publication is Organic Process Research & Development (2019), 23(4), 619-628, database is CAplus.

An advanced process for large scale (500 g) preparation of a (3Z,5Z)-2,7-dihydro-1H-azepine-derived chiral tridentate ligand (Hamari ligand), widely used for asym. synthesis of tailor-made α-amino acids via the corresponding glycine Schiff base Ni(II) complex, is disclosed. The process includes amidation, bis-alkylation, and precipitation/purification of the target compound by TFA as a counterion.

Organic Process Research & Development published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C11H14O4, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ma, Baode published the artcileA new class of tunable dendritic diphosphine ligands. Synthesis and applications in the Ru-catalyzed asymmetric hydrogenation of functionalized ketones, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Chemistry – A European Journal (2014), 20(32), 9969-9978, database is CAplus and MEDLINE.

A series of tunable G₀-G₃ dendritic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four Ph rings on the P atoms. Their ruthenium complexes were employed in the asym. hydrogenation of β-keto esters, α-keto esters, and α-keto amides to reveal the effects of dendron size on the catalytic properties. The absolute configuration of (methyl(phenyl)amino)-1-oxo-butan-2-yl 4-bromobenzoate was determined by the single crystal x-ray diffraction anal. and its data were deposited at the Cambridge Crystallog. Data Center as supplementary publication number CCDC 987977. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small mol. catalysts and the first-generation catalyst. Mol. modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.

Chemistry – A European Journal published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ao, Chunyan published the artcileThe development of new amine-amide ligands for application in Cu(II)-catalyzed enantioselective Henry reactions, Related Products of esters-buliding-blocks, the publication is Tetrahedron: Asymmetry (2016), 27(13), 589-595, database is CAplus.

A new type of chiral tertiary amine ligand was designed and derived from L-proline and (R)-BINOL. These new chiral ligands chelated with Cu(II) showed highly catalytic efficiency in enantioselective Henry reactions. Excellent yields (up to 99%) and high enantioselectivities (up to 96% ee) were achieved for aromatic, hetero-aromatic and aliphatic aldehyde substrates, without an addnl. base additive or the need for air or moisture exclusion.

Tetrahedron: Asymmetry published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, Related Products of esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ikunaka, Masaya published the artcileA Scalable Synthesis of (R)-3,5-Dihydro-4H-dinaphth[2,1-c:1’2′-e]azepine, SDS of cas: 126613-06-7, the publication is Organic Process Research & Development (2003), 7(5), 644-648, database is CAplus.

Environmentally benign scalable procedures are developed to supply enantiomerically pure (R)-3,5-dihydro-4H-dinaphth[2,1-c:1’2′-e]azepine as its hydrogen oxalate salt in a five-step overall yield of 41%, which consist of the following: (1) bis O-triflation of (R)-1,1′-bi-2-naphthol [(CF₃SO₂)₂O, pyridine, PhMe; quant. yield]; (2) Kumada’s cross-coupling [MeMgI, NiCl₂(dppp), tert-BuOMe; 96% yield]; (3) radical bromination [N-bromosuccinimide, 2,2′-azobisisobutyronitrile, cyclohexane; 54% yield]; (4) cyclization [allylamine, Et₃N, THF, 86%]; (5) N-deallylation [1,3-dimethylbarbituric acid, Pd(OAc)₂, Ph₃P, PhMe] followed by crystalline salt formation with oxalic acid (overall 92% yield).

Organic Process Research & Development published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, SDS of cas: 126613-06-7.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Nareddy, Pradeep published the artcileAtropoisomeric (P,N) Ligands for the Highly Enantioselective Pd-Catalyzed Intramolecular Asymmetric α-Arylation of α-Branched Aldehydes, COA of Formula: C22H12F6O6S2, the publication is Angewandte Chemie, International Edition (2012), 51(16), 3826-3831, S3826/1-S3826/106, database is CAplus and MEDLINE.

A short synthetic route readily gives access to a new class of chiral (P,N) ligands characterized by three distinct elements of chirality: axial, central at C and central at P. These ligands are highly enantioselective in Pd-catalyzed intramol. asym. α-arylation of α-branched aldehydes [e.g., I → II].

Angewandte Chemie, International Edition published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, COA of Formula: C22H12F6O6S2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Dotta, Pascal published the artcileDialkyl Effect on Enantioselectivity: π-Stacking as a Structural Feature in P,N Complexes of Palladium(II), Category: esters-buliding-blocks, the publication is Organometallics (2002), 21(14), 3033-3041, database is CAplus.

A phosphino,oxazoline P,N-bidentate ligand, 4, containing 3,5-di-tert-butylphenyl groups was prepared In the Heck arylation of dihydrofuran, 4 affords higher ee’s than either 2 or 3, the unsubstituted and m-dimethylphenyl analogs, resp. Several Pd(0) complexes of 4 are reported. The exchange dynamics of Pd(4)(dba) involve an interconversion of diastereomers via an intramol. process. The x-ray structure for PdCl₂(4), 8, was determined by x-ray diffraction methods. Comparison of data with PdCl₂(2), 9, and PdCl₂(3), 10, suggests that differing amounts of π-π stacking influence the structures of these relatively simple Pd complexes, with 9 and 10 revealing the strongest π-π interactions. An estimation of the van der Waals energies involved in the interaction supports a ∼ 4 kcal/mol stabilization via π-π stacking.

Organometallics published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Lei, Zhi-Yu published the artcileA fast catalytic asymmetric aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone in the presence of chiral bifunctional phosphane Lewis bases, Formula: C22H12F6O6S2, the publication is European Journal of Organic Chemistry (2008), 3817-3820, S3817/1-S3817/52, database is CAplus.

A series of novel bifunctional chiral phosphane Lewis bases having one Ph group and an electron-donating alkyl group on the phosphorus atom was designed and successfully synthesized. The use of these bifunctional chiral phosphane Lewis bases in catalytic asym. aza-Morita-Baylis-Hillman reactions (aza-MBH reactions) of N-sulfonated imines with Me vinyl ketone affords the corresponding adducts in good-to-excellent yields and moderate-to-good enantioselectivities within a few hours at room temperature To the best of our knowledge, this is the fastest catalytic asym. MBH reaction reported thus far.

European Journal of Organic Chemistry published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, Formula: C22H12F6O6S2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics