3594-94-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-BINOL is used as a chiral ligand for [asymmetric synthesis] to facilitate the production of enantiomerically pure pharmaceuticals. Its ability to induce chirality in organic reactions is crucial for creating the desired enantiomers, which are essential for the development of effective and safe medications.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-BINOL is utilized as a chiral ligand for [enantioselective catalysis] to synthesize chiral agrochemicals with improved selectivity and reduced environmental impact. The enantiomeric purity of these compounds is vital for their effectiveness and safety in agricultural applications.
Used in Fine Chemicals Synthesis:
(S)-BINOL serves as a chiral ligand for [asymmetric synthesis] in the preparation of various fine chemicals. Its unique structure and reactivity enable the production of high-quality enantiopure compounds, which are valuable in the fragrance, flavor, and specialty chemical industries.
Used in Enantioselective Catalysis:
(S)-BINOL is employed as a chiral ligand for [enantioselective catalysis] in organic chemistry research and development. Its role in enantioselective catalysis allows for the creation of novel compounds with high enantiomeric purity, which is essential for the advancement of chemical science and technology.

Upstream product

• 18531-96-9 (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 98834-92-5 (S)-2,2'-Bis-1,1'-binaphthyl 
• 99636-47-2 [1,1']Binaphthalenyl-2,2'-dicarboxylic acid dinaphthalen-2-yl ester 
• 77196-14-6 (SS)-tetranaphtho<2,1-b:1,2-d:1,2-h:1,2-j><1,6>dioxacyclododeca-2,4,8,10-tetraene-7,12-dione 
• 77196-14-6 C₄₂H₂₄O₄ 
• 78038-79-6 (+/-)-2,2'-bis(hydroxymethyl)-1,1'-binaphthyl 
• 37803-02-4 (S)-2,2'-bis(bromomethyl)-1,1'-binaphthyl 

Downstream Products

• 18531-96-9 (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid 

Relevant academic research and scientific papers

Solution-phase synthesis and evaluation of tetraproline chiral stationary phases

A protocol was developed for the solution-phase synthesis of multigram amounts of two 9-fluorenylmethoxycarbonyl (Fmoc)-protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution-phase-synthesized tetraproline CSPs with that prepared by stepwise solid-phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs. Copyright

Combinatorial approach for the design of new, simplified chiral phase-transfer catalysts with high catalytic performance for practical asymmetric synthesis of α-alkyl-α-amino acids

A very efficient, chiral phase-transfer catalyst (S)-2Db was prepared by taking advantage of the combinatorial approach from the known, easily available (S)-1,1′-binaphthyl-2,2′-dicarboxylic acid. This catalyst exhibited the high catalytic performance (0.

Reductive ring opening of dihydrodibenzothiepine and dihydrodinaphtho- oxepine and -thiepine

The 4,4′di-tert-butylbiphenyl (DTBB)-catalysed lithiation of dihydrodibenzothiepine (1) at -78°C for 30 min followed by reaction with a carbonyl compound [tBuCHO, Ph(CH2)2CHO, PhCHO, (n-C5H11)2/

Facile synthesis of enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acid via lipase-catalyzed kinetic resolution

Enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acids (R)-1 and (S)-1 have been synthesized through the lipase-catalyzed kinetic resolution of the racemic 2,2-bis(hydroxymethyl)-1,1'-binaphthyl (±)-2 and subsequent oxidation of the hydroxymethyl groups. (C) 2000 Elsevier Science Ltd.

C2 Symmetric Amines. II. Asymmetric Synthesis of C2 (3S,3'S)-and (3R,3'R)Dimethyl 4H-DinaphthAzepines

The C2-symmetric dimethyl amines (1a, 1b) were prepared in high stereoselectivity by carbanion alkylation of their respective formamidines.

The Ullmann Coupling Reaction of Axially Chiral (S)-2,2'-Bis(1-iodo-2-naphtyloxycarbonyl)-1.1'-binaphthyl

The intramolecular Ullmann coupling of the title diester proceeded in low yield but with virtually complete asymmetric induction in joining the two naphthyl units leading to the 12-membered cyclic diester of (S,S)-configuration, which is the same diastereoisomer obtained from the reaction of (S)-2,2'-bis(1-bromo-2-naphthoyloxy)-1,1'-binaphthyl.

The Asymmetric Ullmann Coupling Reaction of Chiral Diol Diesters of 1-Bromo-2-naphthoic Acid and 2-Halo-3-nitrobenzoic Acids: Highly Diastereoselective Synthesis of Atropisomeric 6,6'-Dinitrodiphenic Acids

The copper-promoted Ullmann reaction of chiral diol diesters of 1-bromo-2-naphthoic acid induced axial dissymmetry into the newly formed 1,1'-binaphthyl bond: chiral diol, apparent net optical yield for the joining of two napphthyl units, and axial chirality induced are as follows: (S)-1,1'-binaphthyl-2,2'-diol, 71percent, S; (1S,2S)-1,2-diphenyl-1,2-ethanediol. 32percent, S; (1R,2R)-1,2-bis(ethoxycarbonyl)-1,2-ethanediol. 33percent.S; (4S,5S)-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane, 3.7percent, R.The reaction of (R)-1,1'-binaphthyl-2,2'-diol esters of 2-halo-3-nitrobenzoic acid gave up to 85percent net optical yield for the c oupling; the intramolecular cyclization proceeded with virtually complete diastereoselectivity to give cyclic diester of R,R-configuration in a 42percent isolated yield.This remarkable stereocontrol is ascribed to the steric requirement of the 12-membered cyclic diester structure containing rigid 1,1'-binaphthyl and 1,1'-biphenyl moiety.

Asymmetric Synthesis of Axially Dissymmetric 1,1-Binaphthyls via an Intramolecular Ullmann Coupling Reaction of (R)- and (S)-2,2'-Bis(1-bromo-2-naphthylcarbonyloxy)-1,1'-binaphthyl

An Ulmann reaction of the chiral bifunctional substrate containing two 1-bromo-2-naphthyl moieties, (S)-2,2'-bis(1-bromo-2-naphthylcarbonyloxy)-1,1'-binaphthyl, gives an intramolecularly coupled 12-membered cyclic diester in a 36 percent isolated yield.The intramolecular coupling reaction prodeeds with virtually complete diastereoselectivity to induce S-chirality into newly formed bond between the two naphthyl units.

Induction of Axial Dissymmetry into the 1,1'-Binaphthyl Bond via an Intramolecular Ullmann Coupling Reaction

Intramolecular Ullmann coupling of (S)-2,2'-bis-(1-bromo-2-naphthylcarbonyloxy)-1,1'-binaphthyl induced axial dissymmetry of the S-configuration into the newly formed 1,1'-binaphthyl linkage affording (S,S)-tetranaphthodioxacyclododecene-11,16-dione with virtually complete diastereoselectivity.