583050-18-4

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-Binaphthalene]-2,2'-diol, 4,4'-diphenyl-, (1S)is used as a chiral building block for the synthesis of various pharmaceuticals. Its ability to impart chirality to molecules makes it a valuable component in the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, [1,1'-Binaphthalene]-2,2'-diol, 4,4'-diphenyl-, (1S)is employed as a chiral building block for the synthesis of agrochemicals. [1,1'-Binaphthalene]-2,2'-diol, 4,4'-diphenyl-, (1S)contributes to the development of more effective and selective pesticides and other agricultural products.
Used in Asymmetric Catalysis:
[1,1'-Binaphthalene]-2,2'-diol, 4,4'-diphenyl-, (1S)is used as a chiral ligand in asymmetric catalysis, particularly in enantioselective hydrogenation reactions. Its role in these reactions is crucial for the production of enantiomerically pure compounds, which are essential in various applications, including pharmaceuticals and agrochemicals.
Used in Chemical Synthesis:
[1,1'-Binaphthalene]-2,2'-diol, 4,4'-diphenyl-, (1S)is also used in the broader field of chemical synthesis, where its chiral properties are harnessed to create a wide range of chiral molecules with specific applications in various industries.
Used in Production of Chiral Auxiliaries:
[1,1'-Binaphthalene]-2,2'-diol, 4,4'-diphenyl-, (1S)is utilized in the production of chiral auxiliaries, which are essential tools in organic chemistry for the synthesis of enantiomerically pure compounds.
Used as a Resolving Agent:
In the field of racemic mixture resolution, [1,1'-Binaphthalene]-2,2'-diol, 4,4'-diphenyl-, (1S)serves as a resolving agent. This application is vital for separating enantiomers, which can have different biological activities and are often required for the development of single-enantiomer drugs.

Upstream product

• 36159-74-7 4-phenylnaphthalen-2-ol 
• 93-91-4 1-phenylbutan-1,3-dione 

Relevant academic research and scientific papers

Copper-catalyzed divergent oxidative pathways of 2-naphthol derivatives:: Ortho -naphthoquinones versus 2-BINOLs

Catalyst-dependent divergent pathways of 2-naphthol derivatives have been investigated. A readily available CuCl2-DMAP catalyst system promotes the aerobic oxidation of 2-naphthol derivatives to ortho-naphthoquinones whereas switching the catalyst system to Cu(OAc)2-DBN under an argon atmosphere allows the oxidative coupling of 2-naphthols to 1,1′-bi-2-naphthols (BINOLs) in good to excellent yields.

SYNTHETIC METHOD FOR CHIRAL BINOL COMPOUNDS

A method for synthesizing a chiral binol-based compound of the present invention comprises a step of occurring an oxidative coupling reaction under oxygen conditions in a naphthol derivative having a hydrogen bond at position 3 of 2-naphthol and one of an alkyl group, a cycloalkyl group, and an aryl group bonded at position 4 with a substituent, thereby allowing to control the synthesis of either (R)-enantiomer or (S)-enantiomer of binol, wherein a mononuclear asymmetric vanadium catalyst is used to manufacture (R)-enantiomer of binol and a heteronuclear asymmetric vanadium catalyst is used to manufacture (S)-enantiomer in the controlling step.COPYRIGHT KIPO 2019

Further Structural Modification of Sulfur-Stabilized Silicon Cations with Binaphthyl Backbones

The synthesis and spectroscopic characterization of two novel cationic silicon-sulfur Lewis pairs with a chiral 4,4′-disubstituted binaphthyl silepine backbone are described. Both Lewis acids induce significant enantioselectivity in the model Diels-Alder reaction of cyclohexa-1,3-diene and chalcone but additional substitution of the binaphthyl backbone exerts a minimal effect on enantioinduction compared to previously reported Lewis acids. Another silicon cation with a chiral spirocyclic backbone induces enantioselectivity in the same range but its synthesis is laborious.

Preparation and catalytic activity of BINOL-derived silanediols

Enantiopure silanediols derived from BINOL are an innovative family of stereoselective hydrogen-bond donor (HBD) catalysts. Silanediols incorporated into a BINOL framework are attractive catalysts, as they are readily accessible and highly customizable. Structural modifications of the BINOL backbone affect the reactivity and selectivity of the silanediol catalysts in the additions of silyl ketene acetals to N-acyl isoquinolinium ions. The best results were obtained when the silanediol scaffold was substituted at the 4,4'- and 6,6'-positions. This report includes details regarding the properties of selected BINOL-based silanediol catalysts, including their acidities, binding constants, and X-ray crystal structures.

Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones

The reaction of 2-(trimethylsilyl)phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselectiv

Tandem carbon-carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: Novel formation of 4,4′-disubstituted 1,1′-binaphthols

An efficient route to 4-aryl-2-naphthols from arynes and aroylacetones was developed by carbon-carbon bond insertion followed by an intramolecular aldol reaction and dehydration. Benzyne derived from 2-(trimethylsilyl)phenyl triflate reacted with benzoyla