208248-66-2

Usage

Uses

Used in Asymmetric Synthesis:
(R)-2,2'-Diamino-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl is used as a chiral ligand in asymmetric synthesis for controlling the stereochemistry of the products. Its chiral nature allows for the selective formation of enantiomers, which is essential in the synthesis of biologically active compounds and pharmaceuticals.
Used in Catalysis:
In the field of catalysis, (R)-2,2'-Diamino-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl serves as a chiral catalyst, facilitating various organic reactions with high enantioselectivity and efficiency. Its ability to control the stereochemistry of reactions makes it a valuable tool in the development of enantioselective catalysts.
Used in Pharmaceutical Industry:
(R)-2,2'-Diamino-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl has been studied for its potential use in the pharmaceutical industry. Its chiral properties make it a promising candidate for the development of chiral drugs, which can exhibit improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Other Industrial Applications:
Beyond its applications in asymmetric synthesis, catalysis, and pharmaceuticals, (R)-2,2'-Diamino-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl also has potential uses in other industrial applications. Its unique structural features and chiral nature can be leveraged in the development of new materials, sensors, and other technologies that require chiral compounds.

Upstream product

• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 

Downstream Products

• 229177-79-1 (R)-2,2'-bis(diphenylphosphinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl 

Relevant academic research and scientific papers

Method for resolving chiral compound

The invention relates to the field of organic chemistry, in particular to a method for resolving a chiral compound. The method for splitting the chiral compound provided by the invention comprises thestep of carrying out addition reaction on a racemic compound shown as a formula A and azodicarbonic acid ester in the presence of a catalyst so as to provide an S-configuration compound shown as theformula A and an S-configuration compound shown as the formula C. According to the method, chiral phosphoric acid is used as a catalyst; good catalytic effect is achieved, and very wide substrate applicability is also achieved; the product and the recovered raw material can be obtained with excellent enantioselectivity, the selectivity coefficient of kinetic resolution can reach 371, and the method has an excellent kinetic resolution effect on various N-monosubstituted and N-unsubstituted binaphthalene diamines, H8-binaphthalene diamines and biphenyl diamines.

A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation

A versatile kinetic resolution of protecting-group-free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. A series of mono-N-protected and unprotected BINAMs, diphenyl diamines and NOBIN derivatives could be kinetically resolved with excellent performances (with s factor up to 420). The gram-scale reactions and facile derivatizations of the chiral products demonstrate the potential of these methods in the asymmetric synthesis of chiral catalysts and ligands.

Process for the preparation of Binaphthylderivaten

The production of H8-1,1'-bi-2-naphthyl derivatives is by selective reduction of a binaphthyl derivative with hydrogen, together with a catalyst containing at least one metal of Pt, Ir, Os, Pd, Rh, Ru, Ni, Co and Fe on a carrier. The production of H8-1,1'

Chiral aminophosphines

This invention relates to (R)- and (S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (R-1 and S-1) and (R)- and (S)-2,2'-bis(diarylphospinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R-2 and S-2) and (R)- and (S)-2,2'-bis(dialkylphospinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R-3 and S-3); to a process for the preparation of R-1 and S-1 in which (R) or (S)-1,1'-binaphthyl-2,2'-diamine is partially hydrogenated in the presence of Adam's catalyst (5-20 wt % of starting material) at 20-100° C. for 20-100 hours in glacial acetic acid (solvent); to a process for the preparation of R-2, S-2, R-3 and S-3 in which R-1 or S-1 is reacted with chlorodiarylphosphine or chlorodialkylphosphine in the presence of n-butyllithium; and to the rhodium complexes containing 2 or 3 as effective catalysts for the asymmetric hydrogenation of prochiral substrates such as olefins to produce higher valued chiral products; and to the asymmetric catalytic hydrogenation of enamides under mild conditions using the Rh-(2) or Rh-(3) as catalyst with chemical yields as high as 100% and enantiomeric excess (e.e.) as high as 99%.