215433-52-6

Basic information

• Product Name: R-3,3'-bis([1,1'-biphenyl]-4-yl)-1,1'-Binaphthalene]-2,2'-diol
• Synonyms: R-3,3'-bis([1,1'-biphenyl]-4-yl)-1,1'-Binaphthalene]-2,2'-diol;(R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'- diol, 99%e.e.;(R)-3,3'-Bis([1,1'-biphenyl]-4-yl)-[1,1'-binaphthalene]-2,2'-diol, 98% (99% ee)
• CAS NO: 215433-52-6
• Molecular Formula: C44H30O2
• Molecular Weight: 590.71
• Mol File: 215433-52-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: R-3,3'-bis([1,1'-biphenyl]-4-yl)-1,1'-Binaphthalene]-2,2'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: R-3,3'-bis([1,1'-biphenyl]-4-yl)-1,1'-Binaphthalene]-2,2'-diol(215433-52-6)
• EPA Substance Registry System: R-3,3'-bis([1,1'-biphenyl]-4-yl)-1,1'-Binaphthalene]-2,2'-diol(215433-52-6)

Safety Data

• Hazardous Substances Data: 215433-52-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BINAPO is utilized as a chiral ligand in asymmetric catalysis for the synthesis of enantiomerically pure compounds, which are essential in the development of pharmaceuticals. Its ability to coordinate with metals and facilitate chemical reactions with high enantioselectivity ensures the production of pharmaceuticals with desired chiral properties, improving their efficacy and reducing potential side effects.
Used in Fine Chemicals Industry:
In the fine chemicals industry, BINAPO serves as a valuable chiral ligand for asymmetric catalysis, enabling the synthesis of high-quality enantiomerically pure compounds used in fragrances, agrochemicals, and other specialty chemicals. Its high enantioselectivity ensures the production of fine chemicals with precise stereochemistry, enhancing their performance and applications.
Used in Development of Eco-friendly Synthetic Methodologies:
BINAPO is employed as a key component in the development of green and sustainable synthetic methodologies. Its use in asymmetric catalysis reduces the need for hazardous chemicals and waste, promoting a cleaner and more environmentally friendly approach to chemical synthesis. This contributes to the overall goal of reducing the environmental impact of chemical production processes.
Used in Academic Research:
BINAPO is also widely used in academic research as a model compound for studying asymmetric catalysis and chiral recognition. Its unique structure and properties provide valuable insights into the mechanisms of enantioselective reactions and the development of new chiral catalysts and ligands. This research contributes to the advancement of knowledge in the field of organic chemistry and the discovery of new applications for chiral compounds.

Upstream product

• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 189518-78-3 (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 
• 5122-94-1 4-biphenylboronic acid 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 75714-60-2 (S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 1150311-10-6 3-[(4-phenyl)phenyl]-2-naphthol 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 

Downstream Products

• 699006-54-7 (R)-2,6-di([1,1'-biphenyl]-4-yl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine-4-oxide 

Relevant articles and documents

Catalytic Enantioselective Nazarov Cyclization

A detailed account of an asymmetric Nazarov cyclization that leads to α-hydroxycyclopentenones bearing either vicinal, all-carbon quaternary centers, or vicinal quaternary and tertiary centers is given. The all-aliphatic examples represent the greatest challenge, as the dienone starting materials are not activated toward cyclization by an aryl group. The rational design and optimization of the substrates in parallel with optimization of the chiral Br?nsted acid catalyst is also described, as well as a series of diastereoselective transformations of a fully substituted cyclopentenone product.

Ligand-accelerated stereoretentive Suzuki-Miyaura coupling of unprotected 3,3′-dibromo-BINOL

An efficient synthesis of the enantiomerically pure 3,3′-bis-arylated BINOL derivatives is accomplished through the palladium-catalyzed Suzuki-Miyaura coupling of the unprotected 3,3′-dibromo-BINOL with complete retention of enantiopurity. The active cata

Diastereomeric resolution of rac -1,1′-bi-2-naphthol boronic acid with a chiral boron ligand and its application to simultaneous synthesis of (R)- and (S)-3,3′-disubstituted 1,1′-bi-2-naphthol derivatives

A new concept of diastereomeric resolution has been developed where a boronic acid functionality was employed as (1) a diastereomeric resolving group with a chiral boron ligand and (2) a masked functional group for further transformation thereafter. This new diastereomeric resolution method was successfully applied to the preparation of both (R)- and (S)-3,3′- disubstituted 1,1′-bi-2-naphthol (BINOL) derivatives in a step-ecomonical manner. Racemic BINOL boronic acid reacted with a commercially available pinene-derived iminodiacetic acid as a chiral boron ligand to generate the two diastereomers in quantitative yields over a gram-scale quantity. After the removal of the chiral boron ligand from the diastereomers under mild conditions, the subsequent Suzuki coupling reaction of the resulting chiral BINOL boronic acids with aryl halides provided a series of both (R)- and (S)-BINOL derivatives in good yields. Further, both resulting diastereomers could be directly applied to the Suzuki coupling reaction without the removal of the chiral ligand.

Asymmetric intramolecular hydroamination of allenes using mononuclear gold catalysts

The intramolecular gold-catalyzed asymmetric hydroamination of allenes was studied by screening a series of mononuclear gold(I) and -(III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried,

Copper(I)-catalyzed asymmetric desymmetrization: Synthesis of five-membered-ring compounds containing all-carbon quaternary stereocenters

A highly stereoselective catalytic alkylation sequence for the synthesis of highly functionalized and versatile five-membered-ring compounds bearing all-carbon quaternary stereocenters was developed. Enantioselective desymmetrization of achiral cyclopentene-1,3-diones was thus executed by chiral Cu-phosphoramidite catalysts. A variety of complicated cyclopentane derivatives can be synthesized with excellent stereoselectivities using a low catalyst loading in a one-pot operation.

Synthesis and structural aspects of N-triflylphosphoramides and their calcium salts'highly acidic and effective Bronsted acids

Recently, 1,1′-bi-2-naphthol (BINOL)-based N-triflylphosphoramides emerged as a new class of potent Bronsted acid catalysts. In this paper we describe the efficient synthesis of various BINOL-based N- triflylphosphoramides and their calcium salts. Furthermore, X-ray crystal structure analysis combined with energy-dispersive X-ray spectroscopy (EDX) measurements confirmed that the synthesised chiral N-triflylphosphoramides are highly acidic metal-free catalysts. Freedom! The synthesis and structure determination of various 1,1′-bi-2-naphthol (BINOL)-based N-triflylphosphoramides and their corresponding calcium salts is presented. A simple acidic treatment of the calcium salts provides the metal-free Bronsted acids (see scheme; Tf=trifluoromethanesulfonyl).

Facile and efficient enantioselective strecker reaction of ketimines by chiral sodium phosphate

A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol% BNPNa (BNP=1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol% para-tert-butylortho-adamantylphenol (PBAP) were introduced into the reaction, up to 96% yield and up to 95% ee (ee=enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from β-acetonaphthone, α-indanone, and α-tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1'-binaphthyl-2,2'-diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications.

ASYMMETRIC-SYNTHESIS CATALYST BASED ON CHIRAL BROENSTED ACID AND METHOD OF ASYMMETRIC SYNTHESIS WITH THE CATALYST

A compound usable as an asymmetric synthesis catalyst which can be easily synthesized without using any metal such as a lanthanoid group element; a method of asymmetric synthesis with the compound; and a chiral compound obtained by the asymmetric synthesis method. A Broensted acid is used as a catalyst in asymmetric synthesis, the chiral Broensted acid being represented by formula (1) below or formula (3) below. The asymmetric synthesis method employs the catalyst. Asymmetric synthesis with the catalyst gives a chiral compound.

Formal total synthesis of (+)-diepoxin σ

The highly oxygenated antifungal anticancer natural product (±)-diepoxin σ was prepared in 10 steps and in 15% overall yield from O-methylnaphthazarin. Highlights of the synthetic work include an Ullmann coupling and a possibly biomimetic oxidative spirocyclization for the introduction of the naphthalene ketal as well as the use of a retro-Diels-Alder reaction to unmask the reactive enone moiety in the naphthoquinone bisepoxide ring system. A novel highly bulky chiral binaphthol ligand was developed for a boron-mediated Diels-Alder reaction that constitutes a formal asymmetric total synthesis of (+)-diepoxin σ.