757190-59-3

Upstream product

• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 123-11-5 4-methoxy-benzaldehyde 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 
• 525585-56-2 (1R,2R,N₁E,N₂E)-N₁,N₂-bis(4-methoxybenzylidene)cyclohexane-1,2-diamine 
• 511259-84-0 (R,R)-N,N'-bis[(4-methoxyphenyl)methylene]-1,2-cyclohexanediamine 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 

Relevant academic research and scientific papers

Selenourea and thiourea derivatives of chiral and achiral enetetramines: Synthesis, characterization and enzyme inhibitory properties

A series of chiral and achiral cyclic seleno- and thiourea compounds bearing benzyl groups on N-atoms were prepared from enetetramines and appropriate Group VI elements in good yields. All the synthesized compounds were characterized by elemental analysis

Machine-Assisted Preparation of a Chiral Diamine Ligand Library and In Silico Screening Using Ab Initio Structural Parameters for Heterogeneous Chiral Catalysts

A ligand library containing 31 chiral diamines was synthesized using a flow-based semiautomatic reductive amination system. These ligands were evaluated in a continuous-flow asymmetric 1,4-addition reaction with a heterogeneous Ni catalyst. Based on the experimental results of ab initio DFT calculations, a prediction model for enantioselectivities was successfully constructed. Furthermore, virtual screening of possible ligands was conducted to identify promising structures, which showed good enantioselectivities in experiments. (Figure presented.).

Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides

A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched products with nitrogen-bearing fully substituted carbon centers.

Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols

A series of N,N′-dialkylated derivatives of (1R,2R)-cyclohexane-1,2-diamine were synthesized, and a new approach to the one-pot preparation of this type of amine was demonstrated. The prepared diamines were used as organocatalysts for the two-step synthesis of α-hydroxy γ-keto esters from arenes, chlorooxoacetates, and ketones; they were also used as chiral ligands for Meervein-Ponndorf-Verley reductions and Henry reactions.

Zinc Acetate-Catalyzed Enantioselective Hydrosilylation of Ketones

Zinc acetate complexes with a chiral diphenylethylenediamine (DPEDA)-derived ligand have been proved to be efficient catalysts for the enantioselective hydrosilylation of aryl ketones. Replacing pyrophoric dialkylzinc with the readily available zinc salt simplifies the procedures and provides excellent conversions (up to >99%) and enantioselectivities (ees up to 97%).

Synthesis and characterisation of Cu(II) complexes bearing N,N′-di(methoxybenzyl)-(R,R)-1,2-diaminocyclohexane as catalysts for the asymmetric nitroaldol reaction

Enantiopure Cu(II) complexes with N,N′-di(p-methoxybenzyl)-(R,R)-1,2- diaminocyclohexane (L1), N,N′-di(m-methoxybenzyl)-(R,R)-1,2- diaminocyclohexane (L2), and N,N′-di(m-methoxybenzyl)-(R,R)-1, 2-diaminocyclohexane (L3) li

Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine

The synthesis of a range of C2-symmetric imidazolinium salts from (1R,2R)-cyclohexane-1,2-diamine, and an evaluation of the reactivity and asymmetric induction of the derived NHCs as catalysts for the asymmetric synthesis of β-lactams, is reported. In this series, optimal enantioselectivity (up to 70% ee) is observed using N-benzyl or N-1-naphthylmethyl-substituted NHCs, consistent with a chiral relay effect operating to dictate the stereochemical outcome of this reaction.

Synthesis of chlorinated biphenyls by Suzuki cross-coupling using diamine or diimine-palladium complexes

Several novel diimines (Salen-type ligands) 2a-2i and their reduced diamine counterparts 3b,3d-3g and 3i form complexes 4a-4i, 5b,5d-5g, and 5i with PdCl2 in DMF or methanol. Using 1 mol-% of the isolated complexes 4e and 5f many polychlorinated biphenyls (PCBs) can be prepared in moderate to excellent yields according to the Suzuki cross-coupling protocol with contact to air. Several 4-acetylbiphenyls prepared by this method can be converted in moderate yields into the corresponding biphenylcarboxylic acids (BCAs) by alkaline cleavage. An X-ray crystal structure determination confirms the structure of complex 5f. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Highly selective R,S-coordination of non racemic (1R,2R)-(1,2-dialkyl)-1,2- diamine cyclohexane derivatives to palladium dichloride

In non-racemic (1R,2R)-(1,2-dialkyl)-1,2-diaminocyclohexane palladium dichloride complexes the C2 symmetry of the diamine ligand is broken, resulting in selective R,S-coordination. The Royal Society of Chemistry.