191480-63-4

Usage

Uses

Used in Chemical Synthesis:
(R,R)-(-)-1,2-DIAMINOCYCLOHEXANE HYDROCHLORIDE is used as a chiral ligand for its ability to facilitate asymmetric synthesis, enhancing the selectivity and yield of desired enantiomers in chemical reactions.
Used in Pharmaceutical Industry:
(R,R)-(-)-1,2-DIAMINOCYCLOHEXANE HYDROCHLORIDE is used as a resolving agent for racemic mixtures, enabling the separation of enantiomers which is crucial for the development of single-enantiomer drugs with improved efficacy and reduced side effects.
Used in Catalyst Preparation:
(R,R)-(-)-1,2-DIAMINOCYCLOHEXANE HYDROCHLORIDE is used as a component in the preparation of chiral catalysts due to its selective metal ion binding, which is essential for catalyzing specific asymmetric reactions.
Used in Asymmetric Catalysis:
(R,R)-(-)-1,2-DIAMINOCYCLOHEXANE HYDROCHLORIDE is used as a catalyst in various chemical reactions such as hydrogenation, isomerization, and reduction, where its chiral nature directs the stereochemistry of the products formed.

InChI:InChI=1/C6H14N2.ClH/c7-5-3-1-2-4-6(5)8;/h5-6H,1-4,7-8H2;1H/t5-,6-;/m1./s1

Upstream product

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 

Downstream Products

• 674285-08-6 (1R,2R)-[N,N'-bis(2',3'-dihydroxybenzylidene)]-1,2-diaminocyclohexane 
• 220044-28-0 N-(2-hydroxy-3,5-di-tert-butylbenzaldehyde)-1-amino-2-cyclohexaneimine 

Relevant academic research and scientific papers

A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions

The (salen)Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen)Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen)Co monomer 1 for each reaction class.

Asymmetric ring opening of epoxides with cyanides catalysed by chiral binuclear titanium complexes

A series of Schiff bases obtained from salicylaldehydes and 3,3′-diformyl-BINOL were synthesized. The complexes of these Schiff bases with Ti(IV) were active for the asymmetric ring opening of epoxides with TMSCN. A mixture of unpurified ligands was found

Highly enantioselective fluorescent recognition of amino acid derivatives by unsymmetrical salan sensors

Novel unsymmetrical salan fluorescent sensors 2a and 2b have been designed and synthesized. The chiral recognition of N-Boc-protected amino acids by 2a and 2b has been investigated. Sensor 2a possesses higher sensitivity and enantioselectivity than sensor 2b does. Job analysis and nonlinear regression results show that 2a can form a 1:1 stoichiometric complex with a N-Boc-protected amino acid. The obtained response selectivities and the association constants indicate that 2a is a highly enantioselective and sensitive fluorescent sensor toward N-Boc-protected amino acids.

Cooperative thiourea-Bronsted acid organocatalysis: Enantioselective cyanosilylation of aldehydes with TMSCN

We report a new thiourea - Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.

Enantioselective catalytic α-alkylation of aldehydes via an S N1 pathway

Primary aminothiourea derivatives are shown to catalyze enantioselective alkylation of α-arylpriopionaldehdyes with diarylbromomethane. Evidence for a stepwise, S N1 mechanism in the substitution reaction induced by anion binding to the catalyst is provided by catalyst structure-activity studies, kinetic isotope effects, linear free-energy relationship studies, and competition experiments.

ISOSELECTIVE POLYMERIZATION OF EPOXIDES

The present invention provides novel bimetallic complexes and methods of using the same in the isoselective polymerization of epoxides. The invention also provides methods of kinetic resolution of epoxides. The invention further provides polyethers with high enantiomeric excess that are useful in applications ranging from consumer goods to materials.

POLYMERIC SALEN COMPOUNDS AND METHODS THEREOF

The present disclosure provides a polymerizable compound of the formula (I) where the R1, R2, R’1, R’2, X1 to X8, Y1, Y2, M and L have any of values as defined in the