Tag: M.W=550-600

Meskova, Michaela published the artcileHighly sterically hindered binaphthalene-based monophosphane ligands: synthesis and application in stereoselective Suzuki-Miyaura reactions, Synthetic Route of 126613-06-7, the publication is Tetrahedron: Asymmetry (2013), 24(15-16), 894-902, database is CAplus.

A series of new sterically hindered (R)-(2′-aryl-1,1′-binaphthalene-2-yl)phosphines with ortho-substituted phenyls as aryl groups were prepared via Negishi monoarylation of enantiopure 2,2′-dibromo-1,1′-binaphthalene followed by lithiation and quenching with diphenylphosphino or dicyclohexylphosphino chloride. These ligands were applied to the stereoselective Suzuki-Miyaura coupling for the preparation of substituted biaryls. The enantioselectivity correlated pos. when increasing the hindrance of the 2′-aryl group of the ligand. Using the best performing diphenylphosphine ligand with a 2,6-dimethoxyphenyl aryl group, various arylnaphthalenes were prepared in high to excellent yields (68-99%) with low to good ee (12-75% ee), the latter being comparable to the best values reported when using other chiral monophosphine ligands.

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, Synthetic Route of 126613-06-7.

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

Kasak, Peter published the artcileElaboration of a novel effective approach to enantiopure functionalized 2,2′-dialkyl-1,1′-binaphthyls by stereoconservative cross-couplings at positions 2 and 2′, Product Details of C22H12F6O6S2, the publication is Tetrahedron Letters (2004), 45(27), 5279-5282, database is CAplus.

The yield and the stereochem. outcome of methylation of chiral 1,1′-binaphthyl-2,2′-dielectrophiles (ditriflate and diiodide) clearly depend on the reactivity of the organometallics used. It was found that only the Negishi reaction of a diiodide allowed direct effective synthesis of non-racemic functionalized C₂-sym. 2,2′-dialkyl-1,1′-binaphthyls I (R = Me, Bn, Et, CH₂CH₂CO₂Me, CH₂CH₂CN).

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, Product Details of C22H12F6O6S2.

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

Kasak, Peter published the artcileStereoconservative cyanation of [1,1′-binaphthalene]-2,2′-dielectrophiles. An alternative approach to homochiral C₂-symmetric [1,1′-binaphthalene]-2,2′-dicarbonitrile and its transformations, HPLC of Formula: 126613-06-7, the publication is Collection of Czechoslovak Chemical Communications (2000), 65(5), 729-740, database is CAplus.

Cyanation of [1,1′-binaphthalene]-2,2′-diiodide and [1,1′-binaphthalene]-2,2′-diyl ditriflate showed reactions with zinc cyanide catalyzed by palladium phosphane complex in DMF to be the most effective procedures with almost complete conservation of stereogenic information by affording a corresponding highly enantiomerically enriched dinitrile (from diiodide in 94% yield, 92% ee). The dinitrile was successfully transformed into [1,1′-binaphthalene]-2,2′-dicarboxylic acid and -2,2′-dicarbaldehyde in high yields (84-87%).

Collection of Czechoslovak Chemical 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, HPLC of Formula: 126613-06-7.

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

Cavazzini, Marco published the artcilePalladium-catalyzed asymmetric allylic alkylation in the presence of a chiral ‘light fluorous’ phosphine ligand, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Chemical Communications (Cambridge, United Kingdom) (2001), 1220-1221, database is CAplus.

The easily accessible, enantiopure (R)-(+)-2-diarylphosphino-2′-alkoxy-1,1′-binaphthyl I bearing three fluorous ponytails is an efficient ligand in the palladium-catalyzed asym. allylic substitution of 1,3-diphenylprop-2-enyl acetate affording chiral products of up to 87% ee.

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

Cai, Dongwei published the artcileSynthesis of Chiral 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) via a Novel Nickel-Catalyzed Phosphine Insertion, Application of (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Journal of Organic Chemistry (1994), 59(23), 7180-1, database is CAplus.

A two-step synthesis of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) from 1,1′-bi-2-naphthol is described. The key step is a cross-coupling reaction of the chiral ditriflate of 1,1′-bi-2-naphthol with diphenylphosphine using Ni catalysis that produces chiral BINAP in 75% yield with no racemization.

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

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

Cai, Dongwei published the artcile(R)-(+)- and (S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (phosphine, [1,1′-binaphthalene]-2,2′-diylbis[diphenyl-, (R)- and (S)), SDS of cas: 126613-06-7, the publication is Organic Syntheses (1999), 6-11, database is CAplus.

Treating 30 mmol (R)-(+)-1,1′-bi-2-naphthol with 70 mmol Tf₂O and 90 mmol pyridine in 60 mL CH₂Cl₂ gave 90% of the chiral ditriflate of the binaphthol. Reaction of 20 mmol of the latter compound with 48 mmol Ph₂PH in presence of 2 mmol NiCl₂(dppe) in 60 mL DMF containing 80 mmol DABCO gave 77% (R)-(+)-BINAP.

Organic Syntheses 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

Vaton-Chanvrier, L. published the artcileChiral recognition of binaphthyl derivatives: a chiral recognition model on the basis of chromatography, spectroscopy, and molecular mechanistic calculations for the enantioseparation of 1,1′-binaphthyl derivatives on cholic acid-bonded stationary phases, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), the publication is Chirality (2001), 13(10), 668-674, database is CAplus and MEDLINE.

In an effort to elucidate the mechanism of chiral discrimination of cholic acid-based stationary phases, the enantiomeric recognition ability of six chiral stationary phases (CSPs), prepared from differently substituted cholic acid derivatives, was evaluated in normal phase HPLC with 1,1′-binaphthyl compounds The influence of structural variations of analytes on retention and enantioselectivity was studied. Particularly high values of enantioselectivity were observed for the binaphthol enantiomers on a CSP prepared from the allyl 7α,12α-dihydroxy-3α-phenylcarbamoyloxy-5β-cholan-24-oate. The complexes of this chiral selector with both enantiomers of binaphthol were studied as models for the interactions responsible for the enantioseparation with the cholic acid-based stationary phases. The 1:1 stoichiometry of the complex in solution was determined by UV titration The chiral selector dissolved in chloroform exhibited a chiral discrimination for the binaphthol in ¹H and ¹³C NMR spectroscopies. Some aromatic proton and carbon resonances of binaphthol were clearly separated into a pair of peaks due to enantiomers in the presence of the chiral selector. Also, from mol. mechanics calculation, a chiral discrimination model is proposed which nicely explains the relevant chromatog. behavior of the 1,1′-binaphthyl derivatives

Chirality 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 C9H7N5O, Recommanded Product: (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate).

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

Senda, Taichi published the artcileRhodium-Catalyzed Asymmetric 1,4-Addition of Organoboron Reagents to 5,6-Dihydro-2(1H)-pyridinones. Asymmetric Synthesis of 4-Aryl-2-piperidinones, HPLC of Formula: 126613-06-7, the publication is Journal of Organic Chemistry (2001), 66(21), 6852-6856, database is CAplus and MEDLINE.

Catalytic asym. synthesis of 4-aryl-2-piperidinones was realized by asym. 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introducing the 4-fluorophenyl group, the use of 4-fluorophenylboroxine and 1 equiv (to boron) of water at 40°C gave the highest yield of the arylation product with high enantioselectivity (98% ee). The (R)-4-(4-fluorophenyl)-2-piperidinone obtained is a key intermediate for the synthesis of (-)-Paroxetine.

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 C7H13NO2, HPLC of Formula: 126613-06-7.

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

Woeste, Thorsten H. published the artcileBINAP versus BINAP(O) in Asymmetric Intermolecular Mizoroki-Heck Reactions: Substantial Effects on Selectivities, Related Products of esters-buliding-blocks, the publication is Chemistry – A European Journal (2011), 17(42), 11914-11918, S11914/1-S11914/25, database is CAplus and MEDLINE.

(R)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) I (R = Ph₂P) and its monophosphine oxide (R)-BINAPO I [R = Ph₂P(:O)] were prepared and compared as ligands in the Mizoroki-Heck reactions of 2,3-dihydrofuran and cyclopentene with Ph triflate and iodobenzene in the presence of Pd(OAc)₂ and Pd₂(dba)₃·dba [dba = (E,E)-dibenzylideneacetone]. The regio- and enantioselectivity of the phenylation of 2,3-dihydrofuran and cyclopentene changed dramatically in the presence of hemilabile BINAP(O) instead of BINAP. The phenylation of 2,3-dihydrofuran gave different regioisomers with nearly complete selectivity when BINAP and BINAPO were used; phenylation of 2,3-dihydrofuran using BINAPO gave (R)-2-phenyl-2,5-dihydrofuran with 98:2 regioselectivity in 18-92% ee, while the use of BINAP as ligand gave (R)-5-phenyl-2,3-dihydrofuran exclusively in 16-80% ee. The phenylation of cyclopentene was more regioselective when BINAPO was used as the ligand than when BINAP was used; the reaction gave product in significantly higher enantioselectivity with BINAP(O) (60% ee) than with BINAP (10% ee). The use of Pd₂(dba)₃·dba instead of Pd(OAc)₂ as the palladium source produced enantioselectivities as high as 86% ee in the phenylation of cyclopentene.

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 C7H13ClNNaO5S, Related Products of esters-buliding-blocks.

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

RajanBabu, T. V. published the artcileHeterodimerization of Olefins. 1. Hydrovinylation Reactions of Olefins That Are Amenable to Asymmetric Catalysis, COA of Formula: C22H12F6O6S2, the publication is Journal of Organic Chemistry (2003), 68(22), 8431-8446, database is CAplus and MEDLINE.

Through a systematic examination of ligand and counterion effects, new protocols for a nearly quant. and highly selective codimerization of ethylene and various functionalized vinylarenes have been discovered. In a typical reaction, 4-bromostyrene and ethylene undergo codimerization in the presence of 0.0035 equiv each of [(allyl)NiBr]₂, triphenylphosphine, and AgOTf in CH₂Cl₂ at -56 °C to give 3-(4-bromophenyl)-1-butene in >98% yield and selectivity. Corresponding reactions with [(allyl)PdX]₂ are much less efficient and less selective and may require further optimization before a viable system can be identified. Another useful protocol that gives comparable yield and selectivity involves the use of a single-component catalyst prepared from allyl 2-diphenylphosphinobenzoate, Ni(COD)₂, and (C₆F₅)₃B. Recognition of a synergistic relationship between a chiral hemilabile ligand (for example, (R)-2-methoxy-2′-diphenylphosphino-1,1′-binaphthyl, MOP) and a highly dissociated counteranion (BARF or SbF₆) in an enantioselective version of the Ni-catalyzed reaction raises the prospects of developing a practical route for the synthesis of 3-arylbutenes. Several pharmaceutically relevant compounds, including widely used 2-arylpropionic acids, can be synthesized from these key intermediates. This reaction appears to be quite general. Synthesis of several new 2-diphenylphosphino-1,1-binaphthyl derivatives, prepared to probe the effect of hemilabile coordination on the efficiency and selectivity of the reaction, are also described.

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, COA of Formula: C22H12F6O6S2.

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