134532-03-9

Usage

Uses

Used in Organic Chemistry:
2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE is used as a key intermediate for the synthesis of BINAP, a chiral ligand, due to its unique structure and properties that facilitate asymmetric catalysis.
Used in Asymmetric Synthesis:
2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE is used as a precursor in the production of chiral compounds, contributing to the development of enantioselective reactions and the creation of complex molecular structures with high stereoselectivity.
Used in Materials Science:
2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE is used as a component in chiral molecular assembly, leveraging its chiral nature to construct materials with specific properties and functions.
Used in Pharmaceutical Industry:
2-AMINO-2'-HYDROXY-1 1'-BINAPHTHALENE is used as a precursor for the synthesis of chiral pharmaceutical compounds, enabling the development of drugs with improved efficacy and selectivity.

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 602-09-5 1,1'-bi-2-naphthol 
• 194-63-8 dinaphtho[2,1-b;1',2'-d]furan 
• 74974-14-4 2,2’-bis(diphenylphosphinoamino)-1,1’-binaphthyl 

Downstream Products

• 137848-28-3 (R)-2-amino-2'-hydroxy-1,1'-binaphthyl 
• 137848-29-4 (S)-(-)-2'-amino-[1,1'-binaphthalene]-2-ol 
• 194-59-2 7H-dibenzo[c,g]carbazole 

Relevant academic research and scientific papers

Novel two-phase oxidative cross-coupling of the two-component molecular crystal of 2-naphthol and 2-naphthylamine

Two-phase reaction of a two-component molecular crystal of 2-naphthol and 2-naphthylamine suspended in aqueous Fe3+ solutions gives a cross-coupling product, 2-amino-2′-hydroxy-1,1′-binaphthalene, with good selectivity.

Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes

The selective FeCl3-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing N,O-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.

A general and facile approach for the synthesis of 2'-functionalized 1,1'-binapthyl-2-ols

A facile and efficient protocol for the synthesis of 2'-functionalized 1,1'-binaphthyl-2-ols has been developed. The C,O-dilithio reagent (2) generated by the reductive ring-opening of binaphthofuran (1) with lithium was treated with the corresponding electrophiles to give 2'-functionalized 1,1'-binaphthyl-2-ols including the halides (3), amine (4), acid (5), aldehyde (6), carbonate (7) or phosphonate (8), respectively, in moderate to good yields.

Chiral enrichment of 2-amino-2'-hydroxy-1,1'-binaphthyl

A new synthetic procedure for the formation of 2-amino-2'-hydroxy-1,1'- binaphthyl, and a new purification procedure through the formation of Schiff bases, purification of the Schiff bases, and breakdown of the Schiff bases through amine exchange, are described. Through the new purification procedure, greater than 99% purity of the compound can be obtained easily and reliably. A set of procedures were examined to compare the efficiency and reliability to resolve 2-amino-2'-hydroxy-1,1'-binaphthyl into enantiomers. A new procedure was discovered to enrich enantiomeric excess from less than 10% to 95-99% in one step. Even a racemic mixture from an achiral procedure can be enriched to 67% e.e. in about 4% yield. The X-ray crystal structure of the racemic mixture [rhombohedral, space group Iba2, a=15.718(2) A, b=21.703(2) A, c=8.5398(9) A, V=2913.2(5) A3, RI=0.0705, Z=8, d(calcd)=1.301 g/cm3, F(000)=1200 e] was solved to elucidate the intriguing behavior of this compound.

A practical synthesis of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN)

A practical synthesis of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) was realized from BINOL through a single step. Its facile purification procedure makes the process amenable for large scale synthesis of NOBIN.

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.

Method for resolving chiral compound

The invention relates to the field of organic chemistry, and in particular, relates to a method for resolving a chiral compound. The method for resolving the chiral compound provided by the inventioncomprises the step of carrying out addition reaction on

A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation

A versatile kinetic resolution of protecting-group-free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. A series of mono-N-protected and unprotected BINAMs, diphenyl diamines and NOBIN derivatives could be kinetically resolved with excellent performances (with s factor up to 420). The gram-scale reactions and facile derivatizations of the chiral products demonstrate the potential of these methods in the asymmetric synthesis of chiral catalysts and ligands.

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

We have developed a catalytic system based on bianthrylbis(thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3:2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.

Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols

An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.