55442-34-7

Usage

Derivative

Binaphthol

Usage

Chiral auxiliary in organic synthesis and asymmetric catalysis

Physical state

White to off-white solid

Solubility

Sparingly soluble in water

Chiral centers

Two

Stereoisomers

Four

Potential applications

Pharmaceuticals, agrochemicals, and materials science

Stereochemical control

Ability to impart stereochemical control in chemical reactions

Upstream product

• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 17324-04-8 3-methyl-naphthalen-2-ol 
• 602-09-5 1,1'-bi-2-naphthol 
• 42167-06-6 3,3'-bis(hydroxymethyl)-2,2'-dihydroxy-1,1'-binaphthyl 
• 55442-34-7 3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 77-78-1 dimethyl sulfate 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 74-88-4 methyl iodide 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 142010-89-7 3,3'-Dimethyl-2,2'-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,1']binaphthalenyl 
• 65355-11-5 (Sa)-3,3'-dimethyl-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 345648-05-7 3,3'-dimethyl-2,2'-dimethoxy-1,1'-dinaphthyl 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 

Downstream Products

• 55515-98-5 (R)-3,3'-dimethyl-1,1'-binaphthalene-2,2'-diol 
• 39648-71-0 3,3’-dimethyl-[1,1’-binaphthalene]-2,2’-diol 
• 201732-49-2 ((P)-bis-3,3'-dimethyl-naphthaleno[1,2-f;2,1-d]-1,3-dioxa-2-phosphacycloheptan-2-yl)-(R,R)-bis(1-phenylethyl)amine 
• 201732-49-2 ((M)-bis-3,3'-dimethyl-naphthaleno[1,2-f;2,1-d]-1,3-dioxa-2-phosphacycloheptan-2-yl)-(R,R)-bis(1-phenylethyl)amine 
• 55442-39-2 Dimethyl-ditosylat 25d' 
• 74292-07-2 C₅₀H₄₄O₆*C₈H₉NO₂*ClHO₄ 
• 1220514-89-5 C₅₇H₅₄O₃P₂ 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 149733-66-4 (R*,R*)-(MeC₁₀H₅O)2W(CHPh) 
• 57585-10-1 4-phenyl-2,3-hexadienoic acid methyl ester 
• 57585-09-8 methyl 4-phenylpenta-2,3-dienoate 
• 201732-49-2 C₃₈H₃₄NO₂P 
• 201732-49-2 (2,6-dimethyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 

Relevant academic research and scientific papers

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields.

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.

An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide-iron(ii) complexes

An enantioselective oxidative coupling of 2-naphthol derivatives is developed with the use of chiral Fe(ii)-diphosphine oxide complexes. Optically active 1,1-bi-2-naphthol derivatives can be synthesized in high yields when a 2?:?1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is used in the presence of t-butyl hydroperoxide as an oxidant. The non-linear effect, X-ray crystal structure and ESI-MS suggest that a 2?:?1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is a pre-catalyst for a Fe(iii)/Fe(iv) redox cycle.

Direct asymmetric reductive amination for the synthesis of (S)-rivastigmine

In this article we demonstrate how asymmetric total synthesis of (S)-rivastigmine has been achieved using direct asymmetric reductive amination as the key transformation in four steps. The route started with readily available and cheap m-hydroxyacetophenone, through esterification, asymmetric reductive amination, N-diphenylmethyl deprotection and reductive amination, to provide the final (S)-rivastigmine in 82% overall yield and 96% enantioselectivity. In the asymmetric reductive amination, catalysed by the iridium–phosphoramidite ligand complex and helped by some additives, the readily prepared 3-acetylphenyl ethyl(methyl)carbamate directly reductively coupled with diphenylmethanamine to yield the chiral amine product in 96% ee and 93% yield.

Photochemical Oxidative Coupling of 2-Naphthols using a Hybrid Reduced Graphene Oxide/Manganese Dioxide Nanocomposite under Visible-Light Irradiation

We describe a simple, cost-effective, efficient, and high-yielding photocatalytic approach for the oxidative self-dimerization of 2-naphthols using a semiconductor–metal hybrid that consists of intercalated manganese dioxide nanoparticles in reduced graphene oxide (rGO/MnO2) under visible-light irradiation. The desired photocatalyst was synthesized in a single step by mixing MnO2 nanoparticles with rGO ultrasonically. The hybrid photocatalyst exhibited a significantly higher activity than neat MnO2 nanoparticles and rGO, which is believed to be because of the synergistic effect of its components. To our knowledge, this hybrid rGO/MnO2 nanocomposite is the first heterogeneous, green photocatalyst for the oxidative coupling of 2-naphthols under mild conditions.

Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights

The evolution of a more reactive chiral vanadium catalyst for enantioselective oxidative coupling of phenols is reported, ultimately resulting in a simple monomeric vanadium species combined with a Br?nsted or Lewis acid additive. The resultant vanadium complex is found to effect the asymmetric oxidative ortho-ortho coupling of simple phenols and 2-hydroxycarbazoles with good to excellent levels of enantioselectivity. Experimental and quantum mechanical studies of the mechanism indicate that the additives aggregate the vanadium monomers. In addition, a singlet to triplet crossover is implicated prior to carbon-carbon bond formation. The two lowest energy diastereomeric transition states leading to the enantiomeric products differ substantially with the path to the minor enantiomer involving greater torsional strain between the two phenol moieties.

Tuning ligand structure in chiral bis(phosphite) and mixed phosphite-phosphinite PCP-palladium pincer complexes

A range of chiral resorcinol bis(phosphite) and phosphite-phosphinite ligands were produced and their propensity to form palladium PCP-pincer complexes examined. The ease of base-assisted C-H palladation of the ligands falls in the order bis(phosphinite)

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.

Highly catalytic asymmetric addition of deactivated alkyl Grignard reagents to aldehydes

[Chemical Equation Presented] Generally used and highly reactive RMgBr reagents were effectively deactivated by bis[2-(N,N-dimethylamino)ethyl] ether and then were employed in the highly enantioselective addition of Grignard reagents to aldehydes. The reaction was catalyzed by the complex of commercially available (S)-BINOL and Ti(O'-Pr)4 under mild conditions. Compared with the other observed Grignard reagents, alkyl Grignard reagents showed higher enantioselectivity and they achieved >99% ee.

Copper-catalyzed enantioselective conjugate addition of Grignard reagents to acyclic enones using monodentate phosphoramidite ligands

Herein, we report efficient catalysts based on phosphoramidites for the asymmetric copper-catalyzed conjugate addition of Grignard reagents to acyclic α,β-unsaturated ketones. A variety of Grignard reagents can be added to aliphatic and aromatic acyclic e