860036-29-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(1R,2R)-N,N'-Dihydroxy-N,N'-bis(3,3,3-triphenylpropionyl)cyclohexane-1,2-diamine is utilized as a chiral ligand in the synthesis of pharmaceuticals, particularly in asymmetric hydrogenation processes. Its chiral properties are crucial for the production of enantiomerically pure compounds, which are essential in the development of effective and safe medications.
Used in Fine Chemicals Production:
In the fine chemicals industry, (1R,2R)-N,N'-Dihydroxy-N,N'-bis(3,3,3-triphenylpropionyl)cyclohexane-1,2-diamine serves as a key intermediate due to its ability to form complexes with various metal catalysts. This feature enhances its applicability in the synthesis of high-value specialty chemicals.
Used in Organic Synthesis:
(1R,2R)-N,N'-Dihydroxy-N,N'-bis(3,3,3-triphenylpropionyl)cyclohexane-1,2-diamine is employed as a chiral ligand in organic synthesis, where its unique structure contributes to the development of novel compounds and the improvement of existing synthetic routes.
Used in Chemical Research:
(1R,2R)-N,N'-Dihydroxy-N,N'-bis(3,3,3-triphenylpropionyl)cyclohexane-1,2-diamine is also valuable in chemical research, where it can be used to study the effects of chirality on reaction mechanisms and to develop new catalytic systems for asymmetric reactions.

Upstream product

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 525585-56-2 (1R,2R,N₁E,N₂E)-N₁,N₂-bis(4-methoxybenzylidene)cyclohexane-1,2-diamine 
• 33166-49-3 3,3,3-triphenylpropionyl chloride 
• 860036-40-4 (R,R)-O,O'-bis(triethylsilyl)cyclohexyl-1,2-dihydroxylamine 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 
• 511259-84-0 (R,R)-N,N'-bis[(4-methoxyphenyl)methylene]-1,2-cyclohexanediamine 
• 860036-37-9 C₂₂H₂₆N₂O₄ 
• 926018-49-7 C₁₂H₂₆N₂O₂Si 

Relevant academic research and scientific papers

Direct N-O bond formation via oxidation of amines with benzoyl peroxide

Herein, we report a general and efficient method for direct N-O bond formation without undesirable C-N bond (amide) formation starting from commercially available amines and benzoyl peroxide. The oxidation of 1,2-diamines to furnish bis-(benzoyloxy)-1,2-diamines is reported for the first time. We found that a significant amount of water (BPO?:?water = 3?:?1) in combination with Cs2CO3 is necessary to achieve high selectivity and yield. The reaction conditions are applicable to a wide range of 1,2-diamine and 1,2-disubstituted-1,2-diamine substrates. Additionally this method is highly applicable to primary and secondary amines. Further, the present method can access chiral bis-hydroxamic acids and bis-hydroxyl amines in just two steps from 1,2-diamines. The reaction conditions are simple, mild and inert atmosphere free. The synthetic potential of this methodology is further demonstrated in the short synthesis of a chiral BHA ligand.

Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation

In this article, we describe the development and preliminary results of our new designed C2-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.

Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum

(Chemical Equation Presented) Excellent yields and enantioselectivities can be achieved in the molybdenum-bishydroxamic acid catalyzed asymmetric oxidation of olefins in air at room temperature with an achiral oxidant (see scheme; acac = acetylacetonate).

Catalytic asymmetric epoxidation

The present invention relates to the synthesis of chiral epoxides via a catalytic asymmetric oxidation of olefins. Additionally, the methodology provides a method of asymmetrically oxidizing sulfides and phosphines. This asymmetric oxidation employs a catalyst system composed of a metal and a chiral bishydroxamic acid ligand, which, in the presence of a stoichiometric oxidation reagent, serves to asymmetrically oxidize a variety of substrates.

Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model

(Chemical Equation Presented) Bishydroxamic acid derivatives are used as ligands for a vanadium catalyst in the preparation of epoxy alcohols (see scheme). The methodology uses aqueous tert-butyl hydroperoxide (TBHP) as an achiral oxidant, low catalyst loading, low reaction temperatures (0°C to room temperature), and simple workup procedures. The reaction is applied to the kinetic resolution of a secondary allylic alcohol and the preparation of small epoxy alcohols. R1, R2, R3: alkyl, aryl, H.