1005173-83-0

Usage

Uses

Used in Coordination Chemistry:
(-)-(S,S)-1,2-bis(2-methylphenyl)ethylene-1,2-diamine is used as a ligand for forming coordinate complexes with transition metals. Its ability to bind to metals and influence the stereochemistry of the resulting complexes makes it a crucial component in the development of new coordination compounds with potential applications in various fields.
Used in Asymmetric Catalysis:
In the field of asymmetric catalysis, (-)-(S,S)-1,2-bis(2-methylphenyl)ethylene-1,2-diamine is employed as a chiral ligand to create enantioselective catalysts. (-)-(S,S)-1,2-bis(2-methylphenyl)ethylene-1,2-diamine's chirality allows it to induce selectivity in catalytic reactions, leading to the production of enantiomerically pure products, which is essential in the synthesis of pharmaceuticals and other chiral molecules.
Used in Synthetic Chemistry:
(-)-(S,S)-1,2-bis(2-methylphenyl)ethylene-1,2-diamine is utilized as a building block and a reagent in synthetic chemistry. Its unique structure and ability to form coordinate complexes make it a valuable component in the synthesis of complex organic molecules and the development of new synthetic pathways.
Used in Pharmaceutical Research:
In pharmaceutical research, (-)-(S,S)-1,2-bis(2-methylphenyl)ethylene-1,2-diamine is used as a chiral ligand in the development of new drugs and drug candidates. Its role in asymmetric catalysis and coordination chemistry aids in the synthesis of enantiomerically pure compounds, which is vital for the discovery and development of effective and safe pharmaceuticals.
Used in Materials Science:
(-)-(S,S)-1,2-bis(2-methylphenyl)ethylene-1,2-diamine is also employed in materials science for the design and synthesis of new materials with unique properties. (-)-(S,S)-1,2-bis(2-methylphenyl)ethylene-1,2-diamine's ability to form coordinate complexes can lead to the development of novel materials with potential applications in areas such as electronics, sensors, and nanotechnology.

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 91854-80-7 o-Toluylaldehyd-imin 

Downstream Products

• 1005173-88-5 (4S,5S)-4,5-bis(2-methylphenyl)imidazolidin-2-one 

Relevant academic research and scientific papers

Mechanistic studies inform design of improved Ti(salen) catalysts for enantioselective [3 + 2] cycloaddition

Ti(salen) complexes catalyze the asymmetric [3 + 2] cycloaddition of cyclopropyl ketones with alkenes. While high enantioselectivities are achieved with electron-rich alkenes, electron-deficient alkenes are less selective. Herein, we describe mechanistic studies to understand the origins of catalyst and substrate trends in an effort to identify a more general catalyst. Density functional theory (DFT) calculations of the selectivity determining transition state revealed the origin of stereochemical control to be catalyst distortion, which is largely influenced by the chiral backbone and adamantyl groups on the salicylaldehyde moieties. While substitution of the adamantyl groups was detrimental to the enantioselectivity, mechanistic information guided the development of a set of eight new Ti(salen) catalysts with modified diamine backbones. These catalysts were evaluated with four electron-deficient alkenes to develop a three-parameter statistical model relating enantioselectivity to physical organic parameters. This statistical model is capable of quantitative prediction of enantioselectivity with structurally diverse alkenes. These mechanistic insights assisted the discovery of a new Ti(salen) catalyst, which substantially expanded the reaction scope and significantly improved the enantioselectivity of synthetically interesting building blocks.

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

Diboron glycol ester as well as preparation method, intermediate and application thereof

The invention discloses diboron glycol ester as well as a preparation method, an intermediate and application thereof. The diboron glycol ester can be used for inducing reductive coupling reaction with imine as a substrate, and the substrate can be obtained by reaction of aldehyde and ammonia and is very easy to obtain and quite low in cost. The product can be separated from a reaction system onlyby acid-base operation without column chromatography purification, and the post-treatment mode is convenient and easy to operate. The yield of the obtained product is high, and protective group operation is not needed. The diboron glycol ester has chirality, the stereoselectivity of the reductive coupling reaction is generally excellent, and 99% ee chiral diamine can be obtained only through simple recrystallization. The diboron glycol ester can be obtained by reacting diol with diboron glycol ester, the diol is convenient to prepare and easy to amplify, the diol can be recycled from a reaction solution through simple acid-base operation, the recovery rate reaches 95%, and the preparation cost is further saved.

Optical resolution of (±)-1,2-bis(2-methylphenyl)ethylene-1,2- diamine as a chiral framework for 2-iminoimidazolidine with 2-methylphenyl pendant and the guanidine-catalyzed asymmetric michael reaction of tert-butyl diphenyliminoacetate and ethyl acrylate

(Chemical Equation Presented) (±)-1,2-Bis(2-methylphenyl)ethylene-1, 2-diamine, prepared from benzil and ammonium acetate, was optically resolved as a chiral framework for 2-(1-benzyl-2-hydroxyethyl)imino-1,3- dimethylimidazolidine with 2-methylphenyl pen