59304-49-3

Upstream product

• 7103-09-5 4-but-1-enylmagnesium bromide 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 98-89-5 Cyclohexanecarboxylic acid 
• 80783-98-8 N-methoxy-N-methylcyclohexanecarboxamide 
• 16090-10-1 cyclohexanecarboxylic acid Li-salt 
• 130012-71-4 Cyclohexyl Methylenecyclopropyl Ketone 
• 5162-44-7 1-bromo-4-butene 

Downstream Products

• 1119827-28-9 4-cyclohexyl-2-methylocta-1,7-dien-4-ol 
• 1119827-27-8 4-cyclohexyl-3-methylocta-1,7-dien-4-ol 
• 1119827-26-7 4-cyclohexylocta-1,7-dien-4-ol 
• 1202815-53-9 (1-cyclohexylpent-4-en-1-yl)amine 
• 1781-83-5 spiro[5.5]undecan-1-one 

Relevant academic research and scientific papers

Selective Synthesis of Z-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones

We report a remote functionalization strategy, which allows the Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. The positional selectivity is controlled by the directionality of the chain walk and is independent of thermodynamic preferences of the resulting silyl enol ether. Our mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which serves as a catalyst resting state and, upon reaction with an alkyl bromide, is converted to [Ni(II)-H] as an active chain-walking/functionalization catalyst, ultimately generating a stabilized η3-bound Ni(II) enolate as the key selectivity-controlling intermediate.

Iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes

Herein, an iron-catalyzed acylation-functionalization of unactivated alkenes with aldehydes via distal group ipso-migration is reported. This strategy overcame the energy barrier and reversibility in the difunctionalization of unactivated alkenes with nuc

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.

Asymmetric Synthesis of Chiral Cyclopentanes Bearing an All-Carbon Quaternary Stereocenter by Zirconium-Catalyzed Double Carboalumination

Herein, we report a zirconium-catalyzed enantio- and diastereoselective inter/intramolecular double carboalumination of unactivated 2-substituted 1,5-dienes, which provides efficient and direct access to chiral cyclopentanes through the generation of two

Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon

Esters, acids and acid chlorides can be converted via the intermediacy of their corresponding Weinreb amides into benzene derivatives that incorporate the original carbonyl carbon as part of the benzene ring. The process involves treatment of the derived Weinreb amides with 3-butenylmagnesium bromide and an allylic Grignard reagent, followed by ring-closing metathesis, dehydration and dehydrogenation. The dehydration-dehydrogenation can be done under acidic conditions with a mixture of TsOH·H2O and DDQ or in two steps with SOCl2/pyridine, followed by treatment with DDQ. Application of the method to carbohydrates provides a convenient route to C-5 aryl pyranosides.

Kinetic resolution of aminoalkenes by asymmetric hydroamination: A mechanistic study

The kinetic resolution of chiral aminoalkenes by hydroamination-cyclization was studied by using 3,3'-bis(triarylsilyl)-substituted binaphtholate rare-earth-metal complexes. The resolution of 1-arylaminopentenes proceeds with high efficiency and high irans-diastereoselectivity, whereas the resolution process of 1-alkylaminopentenes suffers from decreasing resolution efficiency with increasing steric demand of the aliphatic substituent. Kinetic studies of the matching and mismatching substrate-catalyst pair by using enantiopure substrates and either the (R)- or (S)-binaphtholate catalysts revealed that the difference in resolution efficiency stems from a shift of the Curtin-Hammett pre-equilibrium. Al-though 1-arylaminopentenes favor the matching substrate-catalyst complex, preference for the mismatching substrate-catalyst complex for 1-alkylaminopentenes diminishes resolution efficiency. Nevertheless, the relative cyclization rate for the two diastereomeric substrate-catalyst complexes remains in a typical range of 7-10:1. Plausible attractive π interactions between the aryl substituent and either the metal center or the aromatic system of the bis(triarylsilyl)-substituted binaphtholate ligand may explain increased sta-bility of the matching substrate-catalyst complex. Incidentally, the methoxymethyl (MOM)-substituted aminopentene 3g also exhibited a strong preference for the matching substrate-catalyst complex, possibly due to the chelating nature of the MOM substituent. The proximity of the stereocenter to the amino group in the aminoalkene substrate was crucial to achieve good kinetic resolution efficiency. The more remote β-phenyl substituent in 2-phenylpent-4-en-l-amine (5) resulted in diminished discrimination of the substrate enantiomers with respect to the relative rate of cyclization of the two substrate-catalyst complexes and a Curtin-Hammett preequilibrium close to unity.

Reductive opening of cyclopropylogous α-hydroxy aldehydes and ketones by samarium(II) iodide

The regioselectivity of the recluctive opening of cyclopropylogous α- hydroxy carbonyl compounds using SmI2 in THF or THF-HMPA was studied and shown to depend strongly on the substrate. In some cases, a tandem cyclopropyl opening-deoxygenation reaction afforded the corresponding γ- keto alkenes in one step.

Synthesis of ketones and aldehydes via reactions of Weinreb-type amides on solid support

Ketones and aldehydes were formed in low to good yields in reactions of Weinreb-type amides on solid support and no overaddition occurred.