63167-00-0

Upstream product

• 823-76-7 Cyclohexyl methyl ketone 
• 100-46-9 benzylamine 
• 4352-49-2 1-cyclohexylethylamine 
• 100-51-6 benzyl alcohol 
• 67404-89-1 N-(1-cyclohexylethyl)benzamide 
• 188645-15-0 N-(1-cyclohexylethylidene)benzylamine 
• 100-52-7 benzaldehyde 
• 5913-13-3 [(1R)-1-cyclohexylethyl]amine 
• 251928-76-4 2-(1-cyclohexyl-vinyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 85970-80-5 1-bromo-1-cyclohexylethylene 
• 931-48-6 2-cyclohexylacetylene 
• 894771-04-1 (R)-2-(1-cyclohexyl-ethyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 622-79-7 benzyl azide 
• 41122-67-2 (R) N-benzylidene-1-cyclohexylethylamine 

Downstream Products

• 1372610-46-2 3-[N-benzyl((R)-1-cyclohexylethyl)amino]-(R)-propane-1,2-diol 
• 1372610-49-5 2-[N-benzyl((R)-1-cyclohexylethyl)amino]-(S)-1-phenoxyethanol 
• 1372610-50-8 2-[N-benzyl((R)-1-cyclohexylethyl)amino]-(R)-1-phenoxyethanol 

Relevant academic research and scientific papers

Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis

The metal-free catalytic hydrogenation of secondary carboxylic acid amides is developed. The reduction is realized by two new catalytic reactions. First, the amide is converted into the imidoyl chloride by triphosgene (CO(OCCl3)2) using novel phosphorus(V) catalysts. Second, the in situ generated imidoyl chlorides are hydrogenated in high yields by an FLP-catalyst. Mechanistic and quantum mechanical calculations support an autoinduced catalytic cycle for the hydrogenation with chloride acting as unusual Lewis base for FLP-mediated H2-activation.

Ultra-small cobalt nanoparticles from molecularly-defined Co-salen complexes for catalytic synthesis of amines

We report the synthesis of in situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt-salen complexes such as cobalt(ii)-N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2-4 nm) cobalt-nanoparticles embedded in a carbon-nitrogen framework. The resulting materials constitute stable, reusable and magnetically separable catalysts, which enable the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds and ammonia. The isolated nanoparticles also represent excellent catalysts for the synthesis of primary, secondary as well as tertiary amines including biologically relevant N-methyl amines.

TRNA SYNTHETASE INHIBITORS

Disclosed herein are secondary amine compounds that inhibit tRNA synthetase. The compounds of the invention are useful in inhibiting tRNA synthetase in Gram-negative bacteria and are useful in killing Gram-negative bacteria. The secondary amine compounds of the invention are also useful in the treatment of tuberculosis.

Chiral molecular tweezers: Synthesis and reactivity in asymmetric hydrogenation

We report the synthesis and reactivity of a chiral aminoborane displaying both rapid and reversible H2 activation. The catalyst shows exceptional reactivity in asymmetric hydrogenation of enamines and unhindered imines with stereoselectivities of up to 99% ee. DFT analysis of the reaction mechanism pointed to the importance of both repulsive steric and stabilizing intermolecular non-covalent forces in the stereodetermining hydride transfer step of the catalytic cycle.

Reductive alkylation of thioamides with Grignard reagents in the presence of Ti(O i Pr)4: Insight and extension

The reductive alkylation of thioamides by Grignard reagents in the presence of Ti(OiPr)4 is the subject of a study involving 20 different substrates. The influence of various parameters has been evaluated, showing notably that the yields of this moderately efficient process can be improved in several cases by applying a slow addition of the Grignard reagent. The results presented in this contribution also provide new insight into the reactivity of the proposed key intermediates, namely, a metalated iminium species and, ultimately, an α-metalated amine. Interestingly, by control of the temperature and the amount of Grignard reagent engaged, the reaction can be directed toward the selective formation of the former titanium intermediate complex. This represents an extension of the original method, allowing the synthesis of various previously inaccessible substituted amines by subsequent addition of a nucleophilic reagent. This role can be played not only by organomagnesium compounds but also by alkyllithium reagents, alkyltitanium(IV) complexes, and lithium aluminum hydride. The properties of the α-metalated amine final intermediate have also been explored, demonstrating that this complex is a poor nucleophile but can act as a radical precursor, which is especially evidenced when the resulting radical species are stabilized. Overall, this chemistry thus proves unexpectedly rich and can plausibly lay the basis for the development of new applications in the future.

Discovery of an iridacycle catalyst with improved reactivity and enantioselectivity in the hydrogenation of dialkyl ketimines

Catalytically active iridacycles are formed by cyclometalation of acetophenone imines with Ir-PHOX complexes under hydrogen atmosphere. These complexes show unusually high reactivity and enantioselectivity in the hydrogenation of alkyl methyl ketimines. T

Asymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenols

A series of novel chiral β-amino alcohols 3-5 and 7-10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34-48 % ee). The ee values of the desired 3-aryloxy-1, 2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of β-blockers and structurally complex molecules.

Asymmetric intermolecular hydroamination of unactivated alkenes with simple amines

A hard nut to crack: The asymmetric intermolecular Markovnikov addition of simple amines to unactivated alkenes can be achieved utilizing binaphtholate rare-earth-metal catalysts with up to 61% ee and 73% de in the case where R 2 contains a stereogenic center.

A bifunctional PdVMgO solid catalyst for the one-pot selective N-monoalkylation of amines with alcohols

It has been found that a bifunctional metal Pd/base (MgO) catalyst performs the selective monoalkylation of amines with alcohols. The reaction goes through a series of consecutive steps in a cascade mode that involves: 1) the abstraction of hydrogen from the alcohol that produces the metal hydride and the carbonyl compound; 2) condensation of the carbonyl with the amine to give an imine, and 3) hydrogenation of the imine with the surface hydrogen atoms from the metal hydride. Based on isotopic and spectroscopic studies and on the rate of each elementary step, a global reaction mechanism has been proposed. The controlling step of the process is the hydride transfer from the metal to the imine. By changing the crystallite size of the Pd, it is demonstrated that this is a structure-sensitive reaction, whereas the competing processes that lead to subproducts are not. On these bases, a highly selective catalyst has been obtained with Pd crystallite size below 2.5 nm in diameter. The high efficiency of the catalytic system has allowed us to extend the process to the one-pot synthesis of piperazines.

Dynamic molecular propeller: Supramolecular chirality sensing by enhanced chiroptical response through the transmission of point chirality to mobile helicity

The secondary terephthalamide host 1a-H attached to four aryl blades was prepared from tetrabromide 2a by Suzuki-Miyaura coupling and undergoes a conformational change from a nonpropeller anti-form to a propeller-shaped syn-form upon complexation with dit