Tag: M.W=550-600

Duclos, Marie-Christine published the artcileSynthesis and evaluation of P-chirogenic monodentate binaphthyl phosphines, Formula: C22H12F6O6S2, the publication is Tetrahedron Letters (2012), 53(45), 5984-5986, database is CAplus.

P-Chirogenic monodentate binaphthyl phosphines were prepared in five steps from enantiomerically pure BINOL. This approach supposes the utilization of two methods previously developed in our group, the formation of secondary phosphine oxide, and the reduction of tertiary phosphine oxide using the association of tetramethyldisiloxane and Ti(OⁱPr)₄. During the last reduction step, only the formation of the more stable diastereoisomer was observed This product was employed as a ligand for the palladium catalyzed hydrosilylation of styrene to afford the corresponding alc. with high yield and enantiomeric excess.

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

Ficks, Arne published the artcileEfficient multigram syntheses of air-stable, chiral primary phosphine ligand precursors via palladium-catalyzed phosphonylation of aryltriflates, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Synthesis (2013), 45(2), 265-271, database is CAplus.

Aryl monotriflates, derived from (R)-BINOL, were alkylated or reduced to give 2′-alkoxy-1,1′-binaphthyl 2-triflates and 1,1′-binaphthyl 2-triflates, resp., which were phosphonylated with HP(O)(OEt)₂ and reduced to the corresponding primary arylphosphines by reaction with LiAlH₄/Me₃SiCl. The prepared 1,1′-binaphthalen-2-ylphosphines are air-stable, chiral primary phosphines, being produced on a multigram scale. The key synthetic step is an optimized palladium-catalyzed phosphonylation reaction of aryl triflates, which opens up a valuable synthetic route to a chiral scaffold that is easily derivatized into novel phosphines.

Synthesis 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

Cho, Suk Young published the artcileSynthesis and evaluation of a new chiral ligand: 2-diphenylarsino-2′-diphenylphosphino-1,1′-binaphthyl (BINAPAs), Related Products of esters-buliding-blocks, the publication is Tetrahedron Letters (1998), 39(13), 1773-1776, database is CAplus.

Chiral 2-diphenylarsino-2′-diphenylphosphino-1,1′-binaphthyl (BINAPAs) was synthesized and is an effective ligand in an aryl triflate-using asym. Heck reaction. For example, intramol. cyclization of I to the tetrahydroanthracene derivative in the presence of BINAPAs, Pd₂(dba)₃ and K₂CO₃ occurred with 91% yield and 88% ee in toluene at 40°.

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, Related Products of esters-buliding-blocks.

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

Zhang, Wen published the artcileAxially chiral P,S-heterodonor ligands with a binaphthalene framework for palladium-catalyzed asymmetric allylic substitutions: experimental investigation on the reversal of enantioselectivity between different alkyl groups on sulfur atom, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Tetrahedron: Asymmetry (2004), 15(21), 3467-3476, database is CAplus.

The enantioselectivity in the palladium-catalyzed asym. allylic alkylation of 1,3-diphenylpropenyl acetate with di-Me malonate using axially chiral P,S-heterodonor ligands BINAPS with different alkyl groups on sulfur atom has been investigated. Their bidentate coordination patterns to a Pd metal center with both P and S atoms have been unambiguously disclosed by X-ray diffraction. The reaction mechanism and the investigation on the reversal of enantioselectivity between different alkyl groups on sulfur atom have been discussed on the basis of the X-ray crystal structure and NMR spectroscopic data.

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 C8H7ClO3, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Zhang, Xiao-Nan published the artcileA Highly Nucleophilic Multifunctional Chiral Phosphane-Catalyzed Asymmetric Intramolecular Rauhut-Currier Reaction, Application In Synthesis of 126613-06-7, the publication is European Journal of Organic Chemistry (2012), 2012(31), 6271-6279, database is CAplus.

An asym. variant of the intramol. Rauhut-Currier (RC) reaction can be achieved using a highly nucleophilic multifunctional chiral phosphine; the corresponding cyclopentene and cyclohexene derivatives are produced in moderate to good yields and with good to excellent enantioselectivities. E.g., in presence of the chiral phosphine I, Rauhut-Currier reaction of (E,E)-II gave 96% cyclohexene derivative III (61% ee).

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 C16H12O, Application In Synthesis of 126613-06-7.

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

Chen, Po-An published the artcileA Binaphthyl-Based Scaffold for a Chiral Dirhodium(II) Biscarboxylate Ligand with α-Quaternary Carbon Centers, Application In Synthesis of 126613-06-7, the publication is ACS Catalysis (2017), 7(9), 6155-6161, database is CAplus.

A nonracemic rhodium(II) paddlewheel complex has been synthesized from binaphthalenedibutanoate biscarboxylate ligands derived from BINOL, and the resulting complex has been used in enantioselective carbene/alkyne cascade reactions. The ligand design was guided by requirements for α,α-di-Me substituted carboxylates and bidentate ligands to ensure high levels of catalytic activity. Previously disclosed chiral complexes lack these features, resulting in low product yields. The design successfully replicated or exceeded the yields of the unusually effective achiral catalyst for the cascade reaction, Rh₂(esp)₂, which often shows unique reactivity. Promising enantioselectivity was observed for the tandem insertion-cyclization reactions of aldehyde-derived hydrazone substrates to give fused bicyclic ethers (29-96% ee), showing that the new scaffold has significant potential.

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

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

Hayashi, Tamio published the artcileRhodium-Catalyzed Asymmetric 1,4-Addition to 1-Alkenylphosphonates, Safety of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Journal of the American Chemical Society (1999), 121(49), 11591-11592, database is CAplus.

Rhodium-catalyzed asym. 1,4-addition is successfully applied to α,β-unsaturated phosphonates by use of triarylcyclotriboroxanes as arylating reagents in place of arylboronic acids. Thus, reaction of (E)-MeCH:CHP(O)(OEt)₂ with phenylboroxine and 1 equivalent (to boron) of water in dioxane at 100° for 3 h gave 94% (S)-di-Et 2-phenylpropylphosphonate.

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

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

Gulyas, Henrik published the artcileHighly active, chemo- and enantioselective Pt-SPO catalytic systems for the synthesis of aromatic carboxamides, Related Products of esters-buliding-blocks, the publication is Catalysis Science & Technology (2015), 5(7), 3822-3828, database is CAplus.

Platinum complexes modified with a chiral non-racemizing SPO pre-ligand have been applied in the hydration of aromatic nitriles. [Pt(1)₃Cl]Cl formed readily from Pt(COD)Cl₂. A chiral secondary phosphine oxide complex showed moderate activity in the hydration of para- and meta-substituted benzonitriles, but failed in converting the ortho-substituted derivatives The hydride complex PtH(PR₂OH)(PR₂O-H···OR₂P) (PR₂OH = 1) formed from Pt(PPh₃)₄ and 1, and the cationic complex derived from [Pt(1)₃Cl]Cl by a direct chloride abstraction with AgNO₃ were proven to be considerably more active, allowing us to extend the scope to the hydration of ortho-substituted aromatic nitriles, including axially chiral [1,1′-binaphthalene]-2,2′-dicarbonitrile. In the hydration of a racemic dinitrile, successful kinetic resolution has been achieved. The catalysts derived from a non-racemizing ligand are the first chiral transition metal-SPO complexes that provide kinetic resolution in the hydration of a racemic chiral nitrile. The synthesis of the target compounds was achieved using (11bR)-4,5-dihydro-3H-Dinaphtho[2,1-c:1′,2′-e]phosphepin 4-oxide as a chiral ligand and dichloro[(1,2,5,6-η)-1,5-cyclooctadiene]platinum or tetrakis(triphenylphosphine)platinum as catalyst. Starting materials included benzonitrile derivatives, naphthalenecarbonitrile, benzeneacetonitrile., [1,1′-binaphthalene]-2,2′-dicarbonitrile.

Catalysis Science & Technology 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

Procter, David J. published the artcileSynthesis of (R)-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]selenepin oxide and preliminary studies on its use in the oxidation of sulfides, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Synthetic Communications (2000), 30(16), 2975-2987, database is CAplus.

The first synthesis of the title compound (R)-I was achieved from (R)-(+)-1,1′-bi-2-naphthol, which in turn was obtained by resolution of rac-1,1′-bi-2-naphthol. Palladium catalyzed alkoxycarbonylation of ditriflate II (R = OSO₂CF₃) gave di-Me ester II (R = COOMe), which was then reduced and the resultant diol converted to key intermediate chloride II (R = CH₂Cl). Cyclization with sodium selenolate gave novel enantiomerically pure selenide, which upon oxidation yielded the desired selenoxide (R)-I. Preliminary studies on the oxidation of sulfides to sulfoxides using I and 2,2,2-trifluoroethanesulfonic acid are also described.

Synthetic Communications 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

Zhao, Luyang published the artcileIntegration of inherent and induced chirality into subphthalocyanine analogue, Application In Synthesis of 126613-06-7, the publication is Scientific Reports (2016), 28026pp., database is CAplus and MEDLINE.

Conventional conjugated systems are characteristic of only either inherent or induced chirality because of synthetic challenge in combination of chiral segment into the main chromophore. In this work, chiral binaphthyl segment is directly fused into the central chromophore of a subphthalocyanine skeleton, resulting in a novel type of chiral subphthalocyanine analog (R/S)-1 of integrated inherent and induced chirality. Impressively, an obviously enhanced optical activity is discerned for (R/S)-1 mols., and corresponding enhancement mechanism is elucidated in detail. The synthesis strategy based on rational mol. design will open the door towards fabrication of chiral materials with giant optical activity, which will have great potential in chiroptical devices.

Scientific Reports 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 C5H11NO2S, Application In Synthesis of 126613-06-7.

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