Category: 126613-06-7

Shi, Min published the artcileChiral Phosphine Lewis Bases Catalyzed Asymmetric aza-Baylis-Hillman Reaction of N-Sulfonated Imines with Activated Olefins, Application of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Journal of the American Chemical Society (2005), 127(11), 3790-3800, database is CAplus and MEDLINE.

In the aza-Baylis-Hillman reaction of N-sulfonated imines (N-arylmethylidene-4-methylbenzenesulfonamides and others) with Me vinyl ketone, Et vinyl ketone, and acrolein, we found that, in the presence of a catalytic amount of chiral phosphine Lewis base such as (R)-2′-diphenylphosphanyl-[1,1′]binaphthalenyl-2-ol LB1 (10 mol %) and mol. sieve 4A, the corresponding aza-Baylis-Hillman adducts could be obtained in good yields with good to high ee (70-95% ee) at low temperature (âˆ?30 to -20 °C) or at room temperature in THF, resp. In CH₂Cl₂ upon heating at 40 °C, the aza-Baylis-Hillman reaction of N-sulfonated imines with Ph acrylate or naphthyl acrylate gave the adducts in good to high yields (60-97%) with moderate ee (52-77%). The mechanistic insight has been investigated by ³¹P and ¹H NMR spectroscopic measurements. The key enolate intermediate, which has been stabilized by intramol. hydrogen bonding, has been observed by ³¹P and ¹H NMR spectroscopy. An effective bifunctional Lewis base and Bronsted acid phosphine Lewis base system has been disclosed in this catalytic, asym. aza-Baylis-Hillman reaction.

Journal of the American Chemical Society 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 C5H6BNO2, Application of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Bayardon, Jerome published the artcileChiral fluorous phosphorus ligands based on the binaphthyl skeleton: synthesis and applications in asymmetric catalysis, Application In Synthesis of 126613-06-7, the publication is Tetrahedron: Asymmetry (2003), 14(15), 2215-2224, database is CAplus.

Two enantiopure fluorous phosphines have been conveniently synthesized by combining palladium-catalyzed coupling reactions of easily available binaphthyl building blocks with the introduction of fluorous ponytails onto aromatic compounds via ether bond formation. These new fluorous chiral phosphines have been tested as ligands in metal-catalyzed asym. transformations, the best results being obtained in the palladium-catalyzed asym. allylic substitution of 1,3-diphenyl-2-propenyl acetate, affording products with up to 87% e.e.

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 In Synthesis of 126613-06-7.

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

Willcox, Darren published the artcileAsymmetric ketone hydroboration catalyzed by alkali metal complexes derived from BINOL ligands, Name: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Dalton Transactions (2020), 49(8), 2417-2420, database is CAplus and MEDLINE.

The ability of alkali metal complexes featuring functionalized BINOL-derived ligands to catalyze ketone hydroboration reactions was explored. The reduced products were formed in excellent yields and with variable enantioselectivities dependent upon the nature of the ligand and the alkali metal cation.

Dalton Transactions 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, Name: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Page, Philip C. Bulman published the artcileBinaphthalene-Derived Iminium Salt Catalysts for Highly Enantioselective Asymmetric Epoxidation, Application In Synthesis of 126613-06-7, the publication is European Journal of Organic Chemistry (2009), 3413-3426, database is CAplus.

Enantiomerically enriched epoxides are useful intermediates that have found many applications in asym. synthesis, and development of efficient catalysts for asym. epoxidation has received considerable attention. In this manuscript we describe the design, preparation, and use of new highly selective iminium salt organocatalysts, e.g. I, for asym. epoxidation, based around a chiral binaphthalene motif coupled with a chiral substituted dioxane moiety. The new catalysts have been tested in the catalytic asym. epoxidation of unfunctionalized alkenes, and provide up to 95 % ee. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009).

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, Application In Synthesis of 126613-06-7.

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

Bulman Page, Philip C. published the artcileIminium salt catalysts for asymmetric epoxidation: the first high enantioselectivities, Quality Control of 126613-06-7, the publication is Organic Letters (2004), 6(10), 1543-1546, database is CAplus and MEDLINE.

A highly enantioselective iminium salt catalyst has been prepared and tested in the catalytic asym. epoxidation of unfunctionalized alkenes, giving up to 95% ee, the highest ee yet reported for iminium salt-catalyzed epoxidation Catalyst loadings as low as 0.1 mol % may be used.

Organic Letters 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, Quality Control of 126613-06-7.

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

Kojima, Akihiko published the artcileSynthesis and evaluation of a new chiral arsine ligand; 2,2′-bis(diphenylarsino)-1,1′-binaphthyl (BINAs), Quality Control of 126613-06-7, the publication is Tetrahedron Letters (1997), 38(19), 3459-3460, database is CAplus.

Chiral 2,2′-bis(diphenylarsino)-1,1′-binaphthyl [(R)-BINAs] was prepared in 34% yield by reaction of Ph₂AsH with (R)-binaphthol ditriflate in DMF containing 10 mol % Ni(COD)₂-dppe. BINAs was an effective ligand in the asym. Heck cyclization of alkenyl iodide I (R = OSiMe₂CMe₃) when 5 mol % Pd₂(dba)₃ was used as catalyst; 90% chem. yield of tetrahydronaphthalene II was obtained with 82% ee.

Tetrahedron Letters 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, Quality Control of 126613-06-7.

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

Han, X. published the artcileSuper/subcritical fluid chromatography separations with four synthetic polymeric chiral stationary phases, Related Products of esters-buliding-blocks, the publication is Chromatographia (2007), 65(7/8), 381-400, database is CAplus.

New synthetic polymeric chiral selectors were developed recently as chiral stationary phases. They were tested with supercritical fluid mobile phases made of CO₂ plus an alc. modifier and 0.2% volume/volume trifluoroacetic acid. The polymeric N,N’-(1S,2S)-1,2-cyclohexanediyl-bis-2-propenamide (P-CAP), the polymeric N,N’-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl] bis-2-propenamide (P-CAP-DP), the polymeric trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide (DEABV) and the polymeric N,N’-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl] bis-4-vinylbenzamide (DPEVB) were bonded to 5 μm silica particles and used to prepare four columns that were tested with a set of 88 chiral compounds with a wide variety of chem. functionalities. All 88 test compounds were separated on one or more of these related polymeric CSPs. Forty-three enantiomeric pairs were separated in SFC conditions by only one of the CSPs. Twenty pairs were separated by two CSPs and 18 and 7 enantiomeric pairs were separated by 3 and all 4 CSPs, resp. The three P-CAP, P-CAP-DP and DEABV CSPs have equivalent success being able to sep. 49 enantiomeric pairs of the studied set with resp. 12, 14 and 20 at baseline (R_s > 1.5). The DPEVB CSP was significantly less efficient separating only 18 chiral compounds with only one at baseline. The great advantage of the SFC mobile phases is the rapid separation, which most achieved in <5 min.

Chromatographia 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

Warner, Christopher J. A. published the artcileEvaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines, Name: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Tetrahedron (2019), 75(50), 130733, database is CAplus.

A series of hydroxy-functionalized bifunctional phosphine oxides and diphosphine dioxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asym. hydrosilylation of ketimines. Bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide (R,R)-Ph(2-MeOC₆H₄)P(CH₂)₆PPh(2-MeOC₆H₄) (32) displayed the highest enantioselectivity of 60%.

Tetrahedron 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 C13H14N2O, Name: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Savary, David published the artcileEnantioselective Pd⁰-catalyzed C(sp²)-H arylation for synthesis of chiral warped molecules, Safety of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Angewandte Chemie, International Edition (2021), 60(10), 5136-5140, database is CAplus and MEDLINE.

C-H activation-based ring-forming methods are a powerful approach for the construction of complex mol. architectures, especially those containing a congested stereo-center. Therefore, this strategy seems perfectly suited to address the synthesis of chiral polycyclic aromatic hydrocarbons (PAHs) and bowl-shaped mols., which are important target mols. in the field of organic electronic materials. Herein, we describe an enantioselective Pd⁰-catalyzed C(sp²)-H arylation protocol for the synthesis of chiral fluoradenes and other warped mols., which could serve to the bottom-up construction of chiral PAHs. The current approach relies on the use of chiral bifunctional phosphine-carboxylate ligands and delivers diverse polycyclic compounds in high yield and with good to excellent enantioselectivity. The chiroptical properties of the obtained products were investigated, and some of them were found to have a strong ellipticity and an emission band located in the visible region.

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, Safety of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Altinel, H. published the artcileNew perfluorinated rhodium-BINAP catalysts and hydrogenation of styrene in supercritical CO₂, Category: esters-buliding-blocks, the publication is Journal of Supercritical Fluids (2009), 51(2), 202-208, database is CAplus.

New perfluorinated BINAP ligands and their cationic rhodium complexes have been synthesized and characterized. The catalysts have been tested in homogeneous hydrogenation of the styrene in both methanol and supercritical carbon dioxide (scCO₂). The selective hydrogenations of the styrene in scCO₂ were carried out under the same reaction conditions of 343.15 K temperature and 120 bar CO₂ pressure after 3 h (molar ratio of substrate to catalyst = 500). While all catalysts showed 100% conversion in methanol, same activity was not carried out in scCO₂. (R)-6,6′-diperflorooctyl-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl-[Rh(COD)]BAr F was showed the highest conversion (96.4%) in scCO₂. Furthermore, methanol was used as co-solvent in the supercritical media in hydrogenation of styrene for the perfluorinated catalysts, which were inactive in scCO₂. Addition of methanol in scCO₂ has rather increased the conversion.

Journal of Supercritical Fluids 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