74292-20-9

Usage

Uses

Used in Organic Chemistry:
(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is used as a key intermediate in the synthesis of various complex organic molecules. Its ability to participate in nickel-catalyzed cross-coupling reactions with aryl Grignard reagents allows for the creation of a wide range of aryl-aryl cross-coupling products, which are essential in the development of new pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is used as a building block for the development of novel drugs. Its unique structure and reactivity enable the synthesis of new drug candidates with potential applications in various therapeutic areas, such as oncology, neurology, and cardiovascular diseases.
Used in Material Science:
(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL is also utilized in the field of material science for the development of advanced materials with specific properties. Its aryl-aryl cross-coupling capability allows for the creation of new materials with tailored electronic, optical, and mechanical properties, which can be applied in various industries, such as electronics, energy, and aerospace.

Upstream product

• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 107-30-2 chloromethyl methyl ether 
• 602-09-5 (R)-binaphthol 
• 13185-00-7 (S)-6,6'-dibromo-1,1'-bi-2-naphthol 
• 109-87-5 Dimethoxymethane 
• 13057-19-7 Iodomethyl methyl ether 

Downstream Products

• 189518-78-3 (S)-2,2’-bis(methoxymethoxy)-3,3’-diiodo-1,1’-binaphthalene 
• 39648-71-0 3,3’-dimethyl-[1,1’-binaphthalene]-2,2’-diol 
• 1621994-95-3 (S)-3-[1-(4-methoxybenzenesulfonyl)-(4S,5S)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]-1,1'-binaphthalene-2,2'-diyl hydrogen phosphate 

Relevant academic research and scientific papers

Enantioselective Au(i)-catalyzed dearomatization of 1-naphthols with allenamides through Tethered Counterion-Directed Catalysis

The Tethered Counterion-Directed Catalysis (TCDC) approach has been applied to the enantioselective Au(i) catalyzed dearomatizations of 1-naphthols with allenamides. Stereocontrol is ensured by the intramolecular ion-pairing between the chiral gold-tether

PROCESS FOR POLYMERIZING BETA-BUTYROLACTONE

A process for polymerizing β-butyrolactone is disclosed comprising contacting racemic β-butyrolactone or an enantiomer thereof with a catalyst/initiator system which comprises a rare earth metal, a chiral ligand, at least one nucleophilic ligand, optional

Chiral Metallacycles as Catalysts for Asymmetric Conjugate Addition of Styrylboronic Acids to α,β-Enones

Introducing self-assembly strategies into the construction of catalysts has been proven to have great advantages in asymmetric catalysis. We constructed two chiral metalla-triangles by highly efficient coordination-driven self-assembly from a chiral 3,3′-dipyridyl-substituted BINOL donor. They were successfully applied in asymmetric conjugate addition of a series of α,β-unsaturated ketones with trans-styrylboronic acids. The use of these metalla-triangles as supramolecular catalysts is obviously conducive to the enhancement of catalytic activity and stereoselectivity in the presented addition reactions. Under induction of the chiral metalla-triangles, an array of α,β-enones were converted to chiral ?,I-unsaturated ketones in medium to quantitative yields (40-98%) with high enantioselectivities (87-96% ee).

Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-Pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis

Tethering a metal complex to its phosphate counterion via a phosphine ligand enables a new strategy in asymmetric counteranion-directed catalysis (ACDC). A straightforward, scalable synthetic route gives access to the gold(I) complex of a phosphine displaying a chiral phosphoric acid function. The complex generates a catalytically active species with an unprecedented intramolecular relationship between the cationic Au(I) center and the phosphate counterion. The benefits of tethering the two functions of the catalyst are demonstrated here in a tandem cycloisomerization/nucleophilic addition reaction, by attaining high enantioselectivity levels (up to 97% ee) at an unusually low 0.2 mol % catalyst loading. Remarkably, the method is also compatible with a silver-free protocol.

Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs

Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.

Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore

A series of axially chiral peri-xanthenoxanthenes (PXXs) were synthesized from 1,1′-bi-2-naphthol without optical resolution. These are the first examples of chiral PXXs. Among them, PXX 5 with two naphthalene rings connected via a methylenedioxy bridge and a chiral axis displayed intense fluorescence (FL) and circularly polarized luminescence (CPL) both in solution (φFL of 0.72 and |glum| of 1.4 × 10-3) and in the solid state (φFL of 0.13 and |glum| of 4.8 × 10-3). The bridged structure of PXX 5 adjusts the angle between the vectors of the electric and magnetic transition dipole moments, which is essential for showing intense CPL activity.

Fluorescent Recognition of 1,3-Diaminopropane in the Fluorous Phase – Greatly Enhanced Sensitivity and Selectivity

A 1,1′-binaphthyl-based dialdehyde, which is soluble in the fluorous phase, is synthesized. The fluorescence of this compound is greatly enhanced by 1,3-diaminopropane (DAP) in perfluorohexane (FC-72) but not by other amines and diamines. Thus, this compound can be used as a fluorescent sensor for the detection of the biologically important DAP at submicromolar concentrations. The selectivity and sensitivity of this fluorescent probe in this fluorous solvent are much greater than those in the common organic solvent dichloromethane.

Click-binol-phosphoric acid catalysts in intramolecular enantioselective oxidative C[sbnd]H-bond functionalization

Counteranion-catalysis represents an appealing but challenging approach for the development of enantioselective oxidative C[sbnd]H bond functionalization reactions. In this work, a new family of 3,3′-triazolyl BINOL-derived phosphoric acids was synthesized and employed in the intramolecular asymmetric C[sbnd]H bond functionalization of N-aryl substituted tetrahydroisoquinolines. As previously reported with related structures, the presence of the triazole groups on the catalysts was key to attain enantioselectivity. Our study also shows the importance of choosing the appropriate regioisomeric triazole groups at the BINOL backbone to achieve a more efficient chirality transfer. Moderate enantiomeric ratios were obtained with the N-benzamide substrates, whereas the change of the nature of the nucleophile fragment was translated to a dramatic loss of the enantioselectivity. Therefore, it can be foreseen that there is a need for designing further superior catalyst structures to develop future counter-anion organocatalyzed asymmetric C[sbnd]H bond functionalization reactions.

A mechanistic study of the Lewis acid-Br?nsted base-Br?nsted acid catalysed asymmetric Michael addition of diethyl malonate to cyclohexenone

The Michael addition of diethyl malonate (Michael Donor, MD) to cyclohexenone (Michael Acceptor, MA) catalysed by the mono-lithium salt of (S)- or (R)-BIMBOL in dichloromethane is shown to exhibit biomimetic behavior. A combination of kinetics, spectrosco

Tree of macromolecule loaded dinaphthol Asia phosphorus amide ligand, its synthetic method and its application

The invention discloses dendrimer polymer loaded binaphthol phosphoramidite ligand and a synthesis method thereof and application of the dendrimer polymer loaded binaphthol phosphoramidite ligand in asymmetric Michael addition reaction of diethyl zinc to