58647-68-0

Upstream product

• 67-56-1 methanol 
• 1821-23-4 1-cyclohex-1-enyl-4-methylbenzene 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 52776-14-4 2-(4-methylphenyl)cyclohexanone 
• 930-68-7 cyclohexenone 
• 5720-05-8 4-methylphenylboronic acid 
• 6729-64-2 tri(p-tolyl)bismuth dichloride 
• 56923-14-9 1-hydroxyimino-2-(4-methylphenyl)-2-cyclohexene 

Downstream Products

• 84211-26-7 semicarbazone of 2e-(4-methylphenyl)-3e-ethylcyclohexanone 
• 1448846-70-5 2-(4-methylphenyl)-6-(ethoxycarbonylmethyl)cyclohex-2-enone 
• 101043-55-4 2-(4-methylphenyl)phenol 
• 52776-14-4 (R)-(-)-2-(4-methylphenyl)cyclohexanone 
• 107388-36-3 (2S,3S)-3-Phenylsulfanyl-2-p-tolyl-cyclohexanone 

Relevant academic research and scientific papers

Asymmetric Hydrogenation of Racemic 6-Aryl 1,4-Dioxaspiro[4.5]decan-7-ones to Functionalized Chiral ?a'Aryl Cyclohexanols via a Dynamic Kinetic Resolution

A ruthenium-catalyzed asymmetric hydrogenation method for the synthesis of functionalized β-aryl cyclohexanols is described. With chiral spiro ruthenium catalyst (Ra,S,S)-5c, a series of racemic α-aryl cyclohexanones bearing a β-monoethylene ketal group were hydrogenated to the corresponding functionalized β-aryl cyclohexanols in high yields with enantioselectivity of up to 99% ee via a dynamic kinetic resolution. This protocol can be conducted on a decagram scale and provide potential approaches for the synthesis of optically active and densely functionalized aryl cyclohexanols.

Dynamic Kinetic Resolution of I-Substituted Cyclic β-Ketoesters via Asymmetric Hydrogenation: Constructing Chiral Cyclic β-Hydroxyesters with Three Contiguous Stereocenters

An efficient asymmetric hydrogenation of racemic I-substituted cyclic β-ketoesters via dynamic kinetic resolution to provide chiral cyclic β-hydroxy esters with three contiguous stereocenters is reported. Using a chiral spiro iridium catalyst (R)-5 (Ir-SpiroSAP), a series of racemic I-Aryl/alkyl substituted cyclic β-ketoesters were hydrogenated to the corresponding chiral cyclic β-hydroxy esters in high yields (84-97%) with good to excellent enantioselectivities (69->99% ee) and cis,cis-selectivities (up to >99:1).

Aqueous chemoenzymatic one-pot enantioselective synthesis of tertiary α-aryl cycloketonesviaPd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation

An aqueous chemoenzymatic cascade reaction combining Pd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation (AH) was developed for enantioselective synthesis of tertiary α-aryl cycloketones in good yields and excellent enantioselectivities. The stereopreference of the enzyme in AH of α-aryl cyclohexenones was studied. An enantiocomplementary enzyme was obtained by site-directed mutation.

Metal-Free I2-Catalyzed Highly Selective Dehydrogenative Coupling of Alcohols and Cyclohexenones

The I2 catalyzed highly selective oxidative condensation of cyclohexenones and alcohols for the synthesis of aryl alkyl ethers has been described. DMSO is employed as the mild terminal oxidant. This novel methodology offers a metal-free reaction condition, operational simplicity and broad substrate scope to afford valuable products from inexpensive reagents. Various meta-substituted aromatic ethers which are hardly synthesized from the reported methods requiring meta-substituted phenols, are efficiently prepared by the present protocol.

A highly efficient metal-free approach to: Meta - And multiple-substituted phenols via a simple oxidation of cyclohexenones

A novel and efficient metal-free approach to substituted phenols has been disclosed from simple and readily available cyclohexenones and cyclohexenone equivalents. Dimethyl sulfoxide (DMSO), a simple and common organic reagent, was employed as a mild oxidant in this I2-catalysis, which significantly tolerates various substituents including some easily oxidizable or reducible functionalities. The challenging meta- and multiple-substituted phenols could be well prepared by this method. The metal-free and mild oxidation make this protocol very simple, practical, and easy to handle.

Versatile CuI/Pd0 dual catalysis for the synthesis of quaternary α-allylated carbonyl compounds: Development, mechanistic investigations and scope

We report herein a versatile cooperative dual catalysis reaction based on a CuI/Pd0 system. Mechanistic investigation shows that every component plays a crucial role in determining the reaction outcome. The reaction is successfully extended to various substrates; such as α,β-unsaturated ketones, malonates and coumarins. The strategy tolerates different substitution patterns and affords good yields for each family of substrates.

Asymmetric hydrogenation of α,α′-disubstituted cycloketones through dynamic kinetic resolution: An efficient construction of chiral diols with three contiguous stereocenters

Chiral diols with three contiguous stereocenters were synthesized by a highly enantioselective ruthenium-catalyzed asymmetric hydrogenation of racemic α,α′-disubstituted cycloketones involving dynamic kinetic resolution. This new catalytic asymmetric method provides a concise route to the alkaloid (+)-γ-lycorane. Copyright

Phosphine Catalyzed α-Arylation of Enones and Enals Using Hypervalent Bismuth Reagents: Regiospecific Enolate Arylation via Nucleophilic Catalysis

Exposure of enones and enals to 20 mol % tributylphosphine in the presence of triarylbismuth(V) dichlorides results in regiospecific aryl transfer to the α-position of the enone or enal pronucleophile. These results represent the first examples of enolate

Modified stille coupling utilizing α-iodoenones

α-Iodoenones undergo Pd-catalyzed coupling with alkenyl- and aryltributylstannanes providing an efficient route to the corresponding α-substituted enones.

Photochemical Reactions of Contact Charge-Transfer Pairs of 1-Arylcyclohexenes and Oxygen

Photoexcitation of contact charge-transfer (CCT) pairs of 1-arylcyclohexenes 1 (aryl: phenyl, 4-methylphenyl, and 4-methoxyphenyl) and oxygen in acetonitrile and benzene gave 1,2-epoxy-1-arylcyclohexanes 2 as major products together with 2-aryl-2-cyclohexen-1-ols and acetophenones 4.Similar irradiation of the CCT pairs in methanol/acetonitrile afforded mainly 2-aryl 2-cyclohexen-1-ones, and 4.The formation of these products can be explained by photoinduced electron transfer in the excited CCT pairs generating radical cations of 1 and superoxide anions.