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Usage

Uses

Used in Asymmetric Synthesis:
(S)-2'-Amino-1,1'-binaphthalen-2-ol is used as a catalyst in the asymmetric synthesis of unnatural α-alkyl amino acids by phase-transfer catalysis (PTC). Its unique structure and properties enable the selective formation of desired enantiomers, which are crucial in the development of pharmaceuticals and agrochemicals.
Used in Catalyst Preparation:
(S)-NOBIN serves as a starting material for the preparation of N-monoalkyl and N,N-dialkyl (S)-NOBIN analogs. These analogs are synthesized by reacting (S)-NOBIN with aldehydes through a reductive amination reaction, further expanding the range of applications for this versatile ligand.
Used in Hartwig-Buchwald Arylation:
(S)-2'-Amino-1,1'-binaphthalen-2-ol is also utilized in the Hartwig-Buchwald arylation reaction to obtain N-monoaryl derivatives. This reaction is an important method for the formation of carbon-carbon and carbon-heteroatom bonds, which are essential in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Chemical Research:
As a red crystalline compound with unique chemical properties, (S)-2'-Amino-1,1'-binaphthalen-2-ol is valuable in chemical research for understanding the behavior of binaphthalene ligands and their potential applications in various chemical processes.

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 134532-03-9 2-amino-2’-hydroxy-1,1’-binaphthyl 
• 6039-59-4 methyl 1-methoxy-2-naphthoate 
• 129656-73-1 (-)-menthyl 1-(-)-menthyloxy-2-naphthoate 
• 116741-64-1 (-)-menthyl (S)-2'-methoxy-1,1'binaphthalene-2-carboxylate 
• 80317-69-7 (aS)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylic acid 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Relevant academic research and scientific papers

Synthesis of new BINAP-based aminophosphines and their 31P-NMR spectroscopy

BINAP aminophosphines are prevalent N,P-bidentate, chiral ligands for asymmetric catalysis. While modification via the BINAP-nitrogen linkage is well explored and has provided a diverse body of derivatives, modification of the other substituents of the phosphorous center is another avenue in generating new congeners of this important class of chiral ligands. Herein reported are new BINAP aryl aminophosphines with electron rich or deficient substituents on the aryl rings. This scalable synthesis converted readily available starting material, (S)-BINOL, to a key intermediate (S)-NOBIN, from which the final chiral aminophosphines were prepared via a palladium-catalyzed, phosphonylation reaction. The aryl substituents are able to modify the electronic properties of the phosphorous center as indicated by the range of 31P-NMR shifts of these new ligands. A computational analysis was performed to linearly quantitate contributions to the 31P-NMR shifts from both resonance and field effects of the substituents. This correlation may be useful for designing and preparing other related aminophosphines with varying ligand properties.

High-yielding large-scale syntheses of enantiomerically pure NOBIN and a NOBIN-based enantiomerically pure NHC precursor

The MOM-protected monotriflate derived from enantiomerically pure (S)-BINOL rendered (S)-NOBIN (67% over 5 steps) and an (S)-configured NHC precursor (55% over 5 steps) on 10 gram and 5 gram scales, respectively. The C-N bond formation was realized by OTf → NHBn and OTf → NH-CH2-CH 2-NH-mesityl exchanges, respectively. Georg Thieme Verlag Stuttgart.

Synthesis and optical properties of (S)-Nobin

A preparative method of synthesis of optically pure S-2-amino-2'-hydroxy-1, 1'-binaphthyl (S-Nobin), the precoursor in the synthesis of other asymmetric 1,1-binaphthyls applied as the ligands at the creation of the catalysts of asymmetric synthesis, is mo

Mechanistic investigations of multidentate organocatalyst-promoted counterion catalysis for fast and enantioselective aza-Morita-Baylis-Hillman reactions at ambient temperature

Kinetic experiments were performed on the catalytic cycle of a trifunctional organocatalyst-promoted counterion catalysis of asymmetric aza-Morita-Baylis-Hillman reactions. The catalysis was found to be first order in the trifunctional catalyst with the Michael addition as the rate-limiting step. Temperature variation changed the rate of catalysis but not the enantioselectivity of the reaction.

Enantioselective catalysis. Part 143: Astonishingly high enantioselectivity in the transfer hydrogenation of acetophenone with 2-propanol using Ru complexes of the Schiff base derived from (S)-2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) and 2-pyridinecarbaldehyde

A series of bidentate and tridentate (S)-NOBIN derivatives was synthesised and tested as chiral ligands in the Ru-catalysed enantioselective transfer hydrogenation of acetophenone with 2-propanol. Despite the similarities in chemical structure, only the imine derived from (S)-NOBIN and 2-pyridinecarbaldehyde and the corresponding amine (obtained by NaBH4 reduction of the imine) afforded (S)-1-phenylethanol in nearly quantitative yields and outstanding enantioselectivities of up to 97% e.e.

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs)

A novel type of chiral redox disulfonate iron complex for asymmetric catalysis is reported. The [Fe((Ra)-BINSate)]+(BINSate = 1,1′-binaphthalene-2,2′-disulfonate) complex effectively promotes the enantioselective oxidative cross-coupling between 2-naphthols (1) and 2-aminonaphthalene derivatives (2), affording optically enriched (Ra)-2-amino-2′-hydroxy-1,1′-binaphthyls (NOBINs) with exceptional yields and enantioselective ratios (up to 99% yield and 96:4 er). The [Fe((Ra)-BINSate)]+catalyst was designed as a chiral version of FeCl3with multicoordination sites available for binding the two coupling partners 1 and 2 as well as the oxidant. Our structure-selectivity and activity study, which covered most of the important positions in the NOBIN scaffold, revealed the effect of different substitution patterns on the coupling efficiency and stereoselectivity.

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.

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