Category: 126613-06-7

Hu, Jian published the artcileHighly active catalysts of bisphosphine oxides for asymmetric Heck reaction, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(82), 9425-9427, database is CAplus and MEDLINE.

Bisphosphine oxides formed highly active asym. Heck catalysts, which were applied in asym. synthesis of pharmacol. active azacycles. E.g., reaction of 2-naphthyl triflate with cyclopentene in the presence of 2.5% Pd(dba)₂ and 3% of chiral ligand, (R)-7-bis(m-xylyl)phosphino-7′-bis(3,5-dimethylphenyl)phosphinyl-1,1′-spirobiindane, in 1,4-dioxane with N-ethyldiisopropylamine at 50° to give 95% yield of (S)-3-(2-naphthyl)cyclopentene. Olefin insertion proceeded via cis pathways, different from P,N-ligands.

Chemical Communications (Cambridge, United Kingdom) 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

Huang, Zhiyan published the artcileAn Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters, Application In Synthesis of 126613-06-7, the publication is Journal of the American Chemical Society (2011), 133(40), 15882-15885, database is CAplus and MEDLINE.

Some examples of enantioselective, intermol. α-arylation of ester enolates with aryl triflates to form tertiary stereocenters using a palladium catalyst supported by a new, (R)-H₈-BINOL-derived monophosphine is presented . The usefulness of the reaction was demonstrated in a gram-scale synthesis of (S)-Naproxen in 92% ee.

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 C22H12F6O6S2, Application In Synthesis of 126613-06-7.

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

Dyke, Alan M. published the artcileDecoupling deprotonation from metalation: Thia-Fries rearrangement, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Angewandte Chemie, International Edition (2008), 47(27), 5067-5070, database is CAplus and MEDLINE.

Studies with ²H-, ¹⁸O-, and ³⁴S-labeled aryl triflates show that lithium diisopropylamide-mediated thia-Fries rearrangement proceeds through an irreversible ortho deprotonation. In contrast, ortho metalation results exclusively in the generation of a benzyne.

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, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Blum, Jochanan published the artcileKinetic resolution of racemic 2,2′-bis(trifluoromethane-sulfonyloxy)-1,1′-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Tetrahedron Letters (1998), 39(31), 5611-5614, database is CAplus.

Kinetic resolution of the racemic title binaphthalene was shown to take place during its methylation with either (Me₂AlOCH₂CH₂OMe)₂ or Me₂Al(CH₂)₃NMe₂ in the presence of an optically active Pd(binap) catalyst, as well as during its alkylation with either (S)-(+)-[Me₂AlOCH₂CH(Me)OCH₂Ph]₂ or (S)-(+)-[Me₂AlOCH₂CH(CH₂CHMe₂)NMe₂]₂ in the presence of an achiral palladium complex to give the Me trifluorosulfonyloxybinaphthalene. The ee values of the resolved binaphthyl derivatives by the two methods were up to 69 and 12%, resp. The latter method represents the first application of a stabilized dialkylaluminum complex with a chiral chelating ligand for asym. induction.

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, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Barta, Katalin published the artcileA new class of 3′-sulfonyl BINAPHOS ligands: modulation of activity and selectivity in asymmetric palladium-catalysed hydrophosphorylation of styrene, HPLC of Formula: 126613-06-7, the publication is Advanced Synthesis & Catalysis (2008), 350(13), 2013-2023, database is CAplus.

Pd-catalyzed mono-phosphorylation of (R)-2,2′-bisperfluoroalkanesulfonates of BINOL (R^F = CF₃ or C₄F₉) by a diaryl phosphinate [Ar₂P(O)H] followed by phosphine oxide reduction (Cl₃SiH) then Li diisopropylamide-mediated anionic thia-Fries rearrangement furnishes enantiomerically-pure (R)-2′-diarylphosphino-2′-hydroxy-3′-perfluoralkanesulfonyl-1,1′-binaphthalenes [(R)-8ab and (R)-8g–j], which can be further diversified by Grignard reagent (RMgX)-mediated CF₃-displacement [→(R)-8c–f]. Coupling of (R)-8a–j with (S)-1,1′-binaphthalene-2,2′-dioxychlorophosphine (S)-9 generates 3′-sulfonyl BINAPHOS ligands (R,S)-10a–j in good yields (43-82%). These new ligands are of utility in the asym. hydrophosphonylation of styrene by 4,4,5,5-tetramethyl-1,3,2-dioxaphospholane 2-oxide, for which a combination of the chiral ligands with either [Pd(Cp)(allyl)] or [Pd(allyl)(MeCN)₂]⁺/NaCH(CO₂Me)₂ proves to be a convenient and active pre-catalyst system. A combination of an electron-rich phosphine moiety and an electron-deficient 3′-sulfone moiety provides the best enantioselectivity to date for this process, affording the branched 2-phenethenephosphonate, (-)-iso-3, in up to 74% ee with ligand (R,S)-10i, where Ar = p-anisyl and the 3′-SO₂R group is triflone.

Advanced Synthesis & Catalysis 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, HPLC of Formula: 126613-06-7.

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

Page, Philip C. Bulman published the artcileNew Chiral Binaphthalene-Derived Iminium Salt Organocatalysts for Asymmetric Epoxidation of Alkenes, Quality Control of 126613-06-7, the publication is Journal of Organic Chemistry (2007), 72(12), 4424-4430, database is CAplus and MEDLINE.

A series of binaphthalene-fused azepinium salts I (R = Me₂CH, Me₃C, n-Bu, cyclohexyl, 2,6-Me₂C₆H₃) has been prepared and used as organocatalysts in the asym. epoxidation of unfunctionalized alkenes, giving rise to ees of up to 84%.

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, Quality Control of 126613-06-7.

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

Ito, Katsuji published the artcileEnantioselective conjugate addition of diethylzinc to acyclic enones using a copper phosphino-phenol complex as catalyst, Formula: C22H12F6O6S2, the publication is Tetrahedron Letters (2005), 46(23), 3981-3985, database is CAplus.

The designed phosphino-phenols I (R = Et, i-Pr, n-Bu, i-Bu, Ph) was found to be an efficient chiral auxiliary for copper-mediated asym. conjugate addition of diethylzinc to acyclic enones. High enantioselectivity was achieved in the reaction of acyclic α,β-enones.

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, Formula: C22H12F6O6S2.

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

D′Arcy, Tom D. published the artcileOrganocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed ortho-Hydroxylative Phenol Dearomatization, HPLC of Formula: 126613-06-7, the publication is Angewandte Chemie, International Edition (2022), 61(30), e202205278, database is CAplus and MEDLINE.

Hydroxylative dearomatization reactions of phenols (HPD) offer an efficient way to assemble complex, biol. relevant scaffolds. Despite this, enantioselective hydroxylative phenol dearomatizations for the construction of bicyclo[2.2.2]octenones are classically limited to stoichiometric chiral reagents, and a practical, enantioselective catalytic method has remained elusive. Herein, authors describe a highly enantioselective, organocatalytic tandem o-HPD-[4+2] reaction. Authors methodol. utilizes a chiral oxaziridinium organocatalyst, that is available in both enantiomeric forms, to afford dearomatized products in high enantioselectivity over a range of phenol substitution patterns. This approach was applied to the highly enantioselective synthesis of (+)-biscarvacrol (99 : 1 e.r.) and (-)-bis(2,6-xylenol) (94 : 6 e.r.). The practicality of authors conditions was demonstrated at gram-scale, using an amine precatalyst, accessible in a single synthetic step.

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, HPLC of Formula: 126613-06-7.

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

Dong, Xing published the artcileEnantioselective hydrogenation of tiglic acid in methanol and in dense carbon dioxide catalyzed by a ruthenium-BINAP complex substituted with OCF₃ groups, Formula: C22H12F6O6S2, the publication is Journal of Molecular Catalysis A: Chemical (2004), 211(1-2), 73-81, database is CAplus.

A fluorinated analog of the 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) ligand was synthesized with OCF₃-substitution of the aryl groups in BINAP skeleton (p-OCF₃-BINAP). Ruthenium complexes of both BINAP (Ru-BINAP) and (p-OCF₃)-BINAP (Ru-[(p-OCF₃)-BINAP]) were also synthesized and investigated as catalysts for hydrogenation of tiglic acid in methanol. Typically, Ru-[(p-OCF₃)-BINAP] had lower activity but had higher enantioselectivity at high hydrogen pressures than Ru-BINAP at the same condition. The effect of OCF₃ groups on the catalytic properties was discussed on the basis of NMR spectra and kinetic data. Ru-[(p-OCF₃)-BINAP] was found to have sufficiently high solubility in dense CO₂ for homogeneous catalytic reactions and was investigated for hydrogenation of tiglic acid in CO₂. The results showed that CO₂ had a great influence on both activity and enantioselectivity. Addition of methanol to CO₂ was found to increase the enantioselectivity.

Journal of Molecular Catalysis A: Chemical 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

Kerrigan, Nessan J. published the artcileStudies in the preparation of novel P-chirogenic binaphthyl monophosphanes (MOPs), Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Tetrahedron Letters (2003), 44(46), 8461-8465, database is CAplus.

Several routes to P-chirogenic binaphthyl monophosphines (MOPs) and their derivatives were investigated. Palladium catalyzed coupling of (R)-1,1′-binaphthyl-2,2′-ditriflate with R¹R²P(O)H in the presence of base gave 2′-(R¹R²-phosphinyl)-1,1-binaphthyl-2-triflate diastereomers (8a,b; R¹ = ^tBu, R² = Ph; 9a,b; R¹ = Ph, R² = 2-MeOC₆H₄). Phosphine oxides 8a and 8b were hydrolyzed, methylated and reduced by Si₂Cl₆ to give corresponding diastereomeric 2-methoxy-2′-methylphenylphosphino-1,1′-binaphthyls (12a,b). The absolute configuration of obtained chiral MOPs was established by x-ray crystallog. Substituents on phosphorus strongly influence the efficiency of the P-C coupling reaction, which is only slightly stereoselective.

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, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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