219583-87-6

Usage

Uses

Used in Pharmaceutical Industry:
S-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene is used as a chiral ligand for [application reason] the synthesis of complex molecules with high stereochemical control, which is essential for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, S-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene is used as a chiral ligand for [application reason] the synthesis of complex molecules with high stereochemical control, contributing to the development of novel agrochemicals with enhanced performance and selectivity.
Used in Academic Research:
S-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene is used as a chiral ligand in academic research for [application reason] the synthesis of complex molecules with high stereochemical control, facilitating the exploration of new chemical reactions and the development of innovative synthetic methods.
Used in New Material Development:
MBI is used as a chiral ligand in the development of new materials for [application reason] its ability to selectively bind to metal ions and form metal complexes, which can be utilized in the creation of advanced materials with unique properties.
Used in Drug Discovery:
S-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene is used as a chiral ligand in drug discovery for [application reason] its potential to enhance the synthesis of complex molecules with high stereochemical control, leading to the identification of novel drug candidates with improved therapeutic profiles.

Upstream product

• 135-19-3 β-naphthol 
• 107-30-2 chloromethyl methyl ether 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 

Downstream Products

• 1352522-61-2 3,3'-bis(1-phenyl-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-63-4 3,3'-bis(1-phenyl-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352522-87-2 3,3'-bis(1-(p-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-88-3 3,3'-bis(1-(p-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352522-91-8 3,3'-bis(1-(p-bromophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-94-1 3,3'-bis(1-(p-bromophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352522-95-2 3,3'-bis(1-(p-fluorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-98-5 3,3'-bis(1-(p-fluorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352523-00-2 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352523-02-4 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 287111-93-7 3,3'-diiodo-[1,1'-binaphthalene]-2,2'-diol 

Relevant academic research and scientific papers

Self-assembly of chiral BINOL cagesviaimine condensation

Condensation of an (S)- or (R)-BINOL-derived dialdehyde and tris(2-aminoethyl)amine produced chiral [2+3] imine cages, which were further reduced to furnish more stable chiral amine cages and applied in the enantioselective recognition of (1R,2R)- and (1S

A crown ether-derived chiral 1, 1 '-linked -2, 2' - naphthol. Preparation method and application thereof

The chiral 1, 1 '-linked -2, 2' - naphthol, 1 1-linked '- and -2 2 naphthol protected by methoxymethyl ether are prepared by reaction of iodine, palladium catalyzed' - Suzuki coupling, hydrolysis, amidation and deprotection. The crown ether-derived chiral 1, 1 '-coupling -2, 2' - naphthol has chirality and steric hindrance, may be a enantiomer, may be a racemate, or may be a racemic mixture of enantiomers. When the chiral 1, 1 '- linked -2 and 2' - naphthol optical purity ≥ 85% ee derived from the crown ether is excellent in effect in asymmetric catalytic reaction, especially asymmetric Michael addition reaction of alkenyl boronic acid and α, β - unsaturated ketone, the optical purity of the product can reach 90%, and high catalytic reaction activity and high activity are achieved 99%. Stereoselectivity.

Br?nsted Acid Catalyzed Stereoselective Polymerization of Vinyl Ethers

Isotactic poly(vinyl ether)s (PVEs) have recently been identified as a new class of semicrystalline thermoplastics with a valuable combination of mechanical and interfacial properties. Currently, methods to synthesize isotactic PVEs are limited to strong

Hypercrosslinking chiral Br?nsted acids into porous organic polymers for efficient heterogeneous asymmetric organosynthesis

Here, we developed a construction strategy for directly immobilizing the axially chiral phosphoric acid into hypercrosslinked polymers by a one-pot Friedel-Crafts alkylation reaction. The obtained chiral polymers have high porosity, excellent stability and tailorable catalytic centers, and display excellent activity, enantioselectivity and recyclability for asymmetric transfer hydrogenation.

Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.

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).

Design and synthesis of a chiral halogen-bond donor with a sp3-hybridized carbon-iodine moiety in a chiral fluorobissulfonyl scaffold

The first example of a chiral halogen-bond donor with a sp3-hybridized carbon-iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from

Br?nsted Acid-Catalyzed Enantioselective Cycloisomerization of Arylalkynes

The first example of an enantioselective carbocyclization of an alkyne-containing substrate catalyzed by chiral Br?nsted acids was achieved. The use of the 2-hydroxynaphthyl substituent on the alkyne as a directing group constituted the key parameter enabling both efficient regioselective protonation of the carbon–carbon triple bond and chiral induction. The key cationic intermediate could be depicted either as a cationic vinylidene ortho-quinone methide or a stabilized vinyl cation. Atropoisomeric phenanthrenes derivatives were produced in high yields and good enantioselectivities under mild, metal-free reaction conditions in the presence of chiral N-triflylphosphoramide catalysts. The carbenic nature of the cationic intermediate was also exploited to describe an example of alkyne/alkane cycloisomerization.

Rhodium-Catalyzed Reaction of Silacyclobutanes with Unactivated Alkynes to Afford Silacyclohexenes

A Rh-catalyzed reaction of silacyclobutanes (SCBs) with unactivated alkynes has been developed to form silacyclohexenes with high chemoselectivity. Good enantioselectivity at the stereogenic silicon center was achieved using a chiral phosphoramidite ligand. The resulting silacyclohexenes are useful scaffolds for synthesizing structurally attractive silacyclic compounds.

The amplified circularly polarized luminescence emission response of chiral 1,1′-binaphthol-based polymers via Zn(II)-coordination fluorescence enhancement

Two kinds of chiral 1,1′-binaphthol (BINOL)-based polymer enantiomers were designed and synthesized by the polymerization of 5,5′-((2,2′-bis (octyloxy)-[1,1′-binaphthalene]-3,3′-diyl)bis(ethyne-2,1-diyl))bis(2-hydroxybenzaldehyde) (M1) with alkyl diamine (M2) via nucleophilic addition–elimination reaction. The resulting chiral polymers can exhibit mirror image cotton effects either in the absence or in the presence of Zn2+ ion. Almost no fluorescence or circularly polarized luminescence (CPL) emission could be observed for two chiral BINOL-based polymer enantiomers in the absence of Zn2+. Interestingly, the chiral polymers can show strong fluorescence and CPL response signals upon the addition of Zn2+, which can be attributed to Zn2+-coordination fluorescence enhancement effect. This work can develop a new strategy on the design of the novel CPL materials via metal-coordination reaction.