79547-82-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol is utilized as a chiral ligand in asymmetric catalysis for the synthesis of pharmaceuticals. Its application is crucial in the production of enantiomerically pure compounds, which are essential for the development of effective and safe medications, as different enantiomers can exhibit distinct biological activities.
Used in Agrochemical Industry:
In the agrochemical sector, (-)-BINOL serves as a chiral ligand in asymmetric catalysis for the synthesis of agrochemicals. This ensures the production of enantiomerically pure active ingredients, which is vital for the effectiveness and selectivity of these chemicals in agricultural applications, reducing potential environmental impact.
Used in Organic Chemistry Research:
(S)-(-)-2-Hydroxy-2'-methoxy-1,1'-bi-naphthol is employed as a chiral ligand in various research applications within organic chemistry. It aids in the exploration of new synthetic pathways and the development of innovative catalytic systems, contributing to the advancement of the field and the discovery of novel compounds with potential applications across various industries.

InChI:InChI=1/C21H20O4/c1-25-19-13-11-15-7-3-5-9-17(15)21(19,24)20(23)16-8-4-2-6-14(16)10-12-18(20)22/h2-13,16-17,22-24H,1H3/t16?,17?,20?,21-/m1/s1

Upstream product

• 35193-70-5 2-hydroxy-2'-methoxy-1,1'-binaphthyl 
• 620-05-3 iodomethylbenzene 
• 1024-41-5 benzyl tosylate 
• 100-39-0 benzyl bromide 
• 602-09-5 1,1'-bi-2-naphthol 

Relevant academic research and scientific papers

Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion

BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C2- and non-C2-symmetric BINOLs. Implementation of this method enables the enantioselective synthesis of a wide range of BINOL derivatives with over 99:1 e.r.

Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols

An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.

Preparative Resolution of Racemates on a Chiral Liquid Chromatography Column

A 2 in. x 30 in. liquid chromatography column packed with a chiral stationary phase derived from (R)-phenylglycine has been found capable of resolving gram or larger samples of a variety of racemates.Nine such resolutions are presented.The racemates resol