96948-51-5

Usage

Uses

Used in Pharmaceutical Synthesis:
R-N, N’-dibenzyl-1,1'-binaphthyldiamine is utilized as a chiral ligand in the synthesis of pharmaceuticals, where its ability to control the stereochemistry of the products is crucial for the development of enantiomerically pure drugs. This ensures the desired biological activity and minimizes potential side effects associated with the less active or unwanted enantiomer.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, R-N, N’-dibenzyl-1,1'-binaphthyldiamine serves as a catalyst to facilitate the formation of chiral centers in organic molecules. Its unique structure allows for the selective formation of one enantiomer over the other, which is essential for the production of biologically active compounds with specific properties.
Used in Biologically Active Compounds Synthesis:
R-N, N’-dibenzyl-1,1'-binaphthyldiamine is employed as a chiral catalyst in the synthesis of biologically active compounds, such as agrochemicals and natural products. Its ability to control the stereochemistry of the products ensures the desired biological activity and selectivity, which is crucial for the effectiveness of these compounds.
Used in Catalyst Development:
In the development of new catalysts for asymmetric reactions, R-N, N’-dibenzyl-1,1'-binaphthyldiamine serves as a starting point or a reference compound. Its well-established catalytic properties and structural features provide insights into the design and optimization of new chiral catalysts for various synthetic applications.
Overall, R-N, N’-dibenzyl-1,1'-binaphthyldiamine is a versatile and valuable compound in the field of synthetic chemistry, with applications spanning across pharmaceuticals, biologically active compounds, and catalyst development. Its unique structure and catalytic properties make it an indispensable tool in the pursuit of enantioselective synthesis and the creation of novel chiral molecules.

Upstream product

• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 100-52-7 benzaldehyde 
• 6653-71-0 N-benzyl-2-bromopropanamide 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 

Relevant academic research and scientific papers

New axially chiral atropos and tropos secondary diamines as ligands for enantioselective intramolecular hydroamination

The highly constrained, axially chiral atropos diamines (Ri,S,S)-1, (Ri,R,R)-1 and (Ri,S,R)-1 and their tropos analogue (Ri)-2 have been prepared via bis-N,N-dialkylation of (R)-2,2′-diamino-1,1′-binaphthyl, using either (R)- or (S)-2,2′-bis(bromomethyl)-1,1′-binaphthyl and 2,2′-bis(bromomethyl)-1,1′-biphenyl as alkylating agents, followed by selective nickel chloride-catalysed bis(mono-hydrogenolysis) of the tertiary amino groups of the so-obtained (Ri,R,R)-4, (Ri,S,S)-4, (Ri,R,S)-4 and (Ri)-6, respectively, by lithium aluminium hydride in refluxing THF or THF/diglyme. The diamines (Ri,S,S)-1, (Ri,R,R)-1, (Ri,S,R)-1 and (Ri)-2 have been evaluated as ligands for ytterbium-catalysed intramolecular hydroamination and compared to the ligand 1,1′-binaphthyl-2,2′-bis(benzylamine) (Ri)-3. They afforded highly active catalysts for the cyclisation of aminopentenes and aminohexenes with up to 58% ee.

Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination

Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec

Chiral aromatic amine compounds and preparation method thereof

The invention discloses chiral aromatic amine compounds and a preparation method thereof. The chiral aromatic amine compounds are characterized in that under the alkaline condition, compounds I reactwith compounds II to obtain corresponding products, namely chiral aromatic amine compounds labeled by compounds with structural formulas III, IV and V or enantiomers, despinners, diastereoisomers or isotopes thereof: (the formula is shown in the description), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and R17 are separately selected from any group, and X is chlorine or bromine. The chiral aromatic amine compounds with high optical purity (an ee value is greater than 99 percent) have wide application in the fields of bioactivity, materials, chiral ligands, chiral catalysts and the like, and can be further derived to prepare recemic or chiral aromatic amine ligands serving as catalyst for asymmetric catalytic reaction. The invention lays a foundation for developing novel catalysts for the asymmetric catalytic reaction and has economic practicality and industrial application prospect.

Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes

A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.

An efficient intermolecular C(aryl)-S bond forming reaction catalyzed by BINAM-copper(II) complex

A wide range of diaryl thioethers and aryl alkyl thioethers are synthesized from the corresponding aryl iodides and aromatic/aliphatic thiols through Ullmann type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-Cu(OTf)2 complex. Less reactive aryl bromides have also been shown to react with thiols under identical reaction conditions to give good yields of the thioethers without increasing the reaction temperature and time.

Chiral diamine-copper(I) complexes as asymmetric catalysts in the enantioselective addition of phenylacetylene to imines

The stereoselective addition of phenyl acetylene to imines, catalysed by chiral bis-amine-Cu(I) complexes was studied. The chiral ligands are either commercially available or easily prepared in one or two steps. This very convenient and extremely simple e