192649-51-7

Usage

Uses

Used in Asymmetric Catalysis:
(R,R)-1,2-Ph2-N,N'-bis(mesitylmethylidene)ethane-1,2-diamine is used as a chiral ligand in transition metal-catalyzed asymmetric reactions for enhancing enantioselectivity and reaction efficiency.
Used in Organic Synthesis:
In the field of organic synthesis, (R,R)-1,2-Ph2-N,N'-bis(mesitylmethylidene)ethane-1,2-diamine is employed as a chiral ligand to facilitate various synthetic transformations, including asymmetric hydrogenation and hydroformylation.
Used in Pharmaceutical Industry:
(R,R)-1,2-Ph2-N,N'-bis(mesitylmethylidene)ethane-1,2-diamine is used as a key intermediate in the synthesis of chiral pharmaceuticals, contributing to the development of more effective and selective drugs.
Used in Chemical Research:
This chiral ligand is also utilized in academic and industrial research for exploring new catalytic processes and advancing the understanding of asymmetric catalysis mechanisms.

Upstream product

• 186769-18-6 (1S,2S)-1,2-di(2,4,6-trimethylphenyl)-1,2-ethanediamine 
• 100-52-7 benzaldehyde 
• 23873-81-6 benzildioxime 
• 487-68-3 mesytaldehyde 
• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 

Downstream Products

• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 
• 138608-02-3 (1R,2R)-1,2-Diphenyl-N,N'-bis-(2,4,6-trimethyl-benzyl)-ethane-1,2-diamine 

Relevant academic research and scientific papers

Stereospecific diaza-cope rearrangement driven by steric strain

(Chemical Equation Presented) Bucklingunder the strain: Steric strain was used to drive the diaza-Cope rearrangement to completion (see scheme) with a high degree of stereospecificity (>99.5% ee), as evidenced by chiral-phase HPLC and crystal data. There is good agreement between the experimental and computational values for the rate and equilibrium constants for the rearrangement.

Organic chemistry: Preparative synthesis of the Corey chiral controller for enantioselective dihydroxylation of olefins

A five-step synthesis of both enantiomers of 1,2-di(2,4,6-trimethylbenzylamino)-1,2-diphenylethane, i.e., Corey (R,R)- and (S,S)-controllers for enantioselective dihydroxylation of olefins by osmium tetroxide, starting from α,α'-diphenylglyoxime, has been developed. The key operations in the synthesis are the optical resolution of intermediate rac-1,2-diamino-1,2-diphenylethane into two enantiomers using only (R,R)-tartaric acid and the subsequent enhancement of the enantiomeric purity to >98% by crystallizations of the corresponding Schiff's bis-bases. Analysis of the enantiomeric purity of the controllers can be easily performed using 1H NMR spectra of their salts with (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (Mosher R-acid).