108368-88-3

Upstream product

• 463-04-7 n-Amyl nitrite 
• 22618-51-5 2'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 16419-60-6 2-Methylphenylboronic acid 
• 930-68-7 cyclohexenone 
• 6957-09-1 1-(2-methylphenyl)-1-cyclohexanol 

Downstream Products

• 1448846-74-9 2-(2-methylphenyl)-6-(ethoxycarbonylmethyl)cyclohex-2-enone 
• 77897-02-0 2-hydroxy-2'-methyl-1,1'-biphenyl 

Relevant academic research and scientific papers

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.

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).

Synthesis of 2-Arylphenol Derivatives through a One-Pot Suzuki-Miyaura Coupling/Dehydrogenative Aromatization Sequence with Pd/C Catalysis

One-pot synthesis of 2-arylphenols starting from 2-iodo-2-cyclohexen-1-one and arylboronic acids through sequential Suzuki-Miyaura coupling/dehydrogenative aromatization with Pd/C catalysis has been developed. A range of arylboronic acids serve as substrates, including those containing electron-donating or electron-withdrawing groups. Additionally, one-pot synthesis of di- or trisubstituted phenols bearing a phenyl group at the ortho position are also generated by using 2-iodo-2-cyclohexen-1-one derivatives as substrate. In the present method, commercially available and easily removable Pd/C was employed as a catalyst without any ligands. The operationally simple procedure and accessible conditions were used to provide modified phenols as the sole product in moderate to high yields.

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

α-Arylation and alkynylation of cyclic -iodoenones using palladium-catalyzed cross-coupling reactions with trifluoroborate salts

An expeditious synthesis of -aryl- and -alkynylcyclohexenones is described and illustrated by palladium-catalyzed cross-coupling reaction of cyclic -iodoenones with potassium aryltrifluoroborate salts. This procedure offers easy access to -arylated and al

Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C

The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(0)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 °C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(0)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.