137273-41-7

Upstream product

• 86487-17-4 2-tri-n-butylstannylanisole 
• 122948-46-3 6-oxocyclohex-1-en-1-yl trifluoromethanesulfonate 
• 578-57-4 2-bromoanisole 
• 77326-17-1 Trimethyl-(7-oxa-bicyclo[4.1.0]hept-2-en-2-yloxy)-silane 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 22618-48-0 1-(cyclohexen-1-yl)-2-methoxybenzene 
• 854913-24-9 2-(2-methoxy-phenyl)-cyclohex-2-enol 
• 6705-49-3 7-oxabicyclo[4.1.0]heptan-2-one 
• 31600-86-9 2-methoxyphenyllithium 

Downstream Products

• 195001-49-1 2-(2'-methoxy)phenyl-1-vinylcyclohex-2-en-1-ol 
• 1027475-48-4 2-(2-Methoxy-phenyl)-3-(1-trimethylsilanyl-vinyl)-cyclohex-2-enol 
• 950585-03-2 (1S,2R)-2-(2-methoxyphenyl)-3-(dimethylphenylsilyl)cyclohexanone 
• 950584-78-8 (2R,3R)-2-(2-methoxyphenyl)-3-(dimethylphenylsilyl)cyclohexanone 
• 950584-77-7 (2S,3S)-2-(2-methoxyphenyl)-3-(dimethylphenylsilyl)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).

The search for tolerant Lewis acid catalysts. Part 2: Enantiopure cycloalkyldialkylsilyl triflimide catalysts

A series of 2-aryl- and arylmethyl-3-dialkylphenylsilyl cycloalkanones have been prepared and resolved. The pure enantiomers were reduced to the corresponding cycloalkane derivatives. These were used for the in situ generation of enantiopure cycloalkylsil

Preparation of 3-oxo-2-cyclohexen-2-ylzinc iodides and their palladium-mediated reactions with aryl or alkenyl halides

2-Iodo-2-cyclohexen-1-ones 10 react under mild conditions with a large excess (4 equiv.) of an activated Zn(Ag) couple in the presence of TMEDA (1 equiv.) leading to the corresponding 3-oxo-2-cyclohexen-2-ylzinc iodides 11 in good yields. These new organo

Use of conjugated dienones in cyclialkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (±)-hinokione, (±)-nimbidiol, sageone, and miltirone

Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

Palladium-Catalyzed Coupling of Arylstannanes with Organic Sulfonates: A Comprehensive Study

The effect of ligands and lithium chloride on the rates of the palladium catalyzed coupling between organic triflates and arylstannanes was studied.The dependence of the rate on the ligand is similar to the one previously reported for the coupling of vinylstannanes, but in the present case triphenylarsine is shown to be superior to both triphenylphosphine and tri(2-furyl)phosphine.The effect of added chloride is complex and varies depending on solvent and ligand used.Ortho-substituted arylstannanes tend to transfer alkyl moieties to a substantial extent, andtherefore rates and efficiencies of aryl vs alkyl transfer were quantitated.When ortho substituents that are potentially coordinating to tin are used, no rate acceleration in the alkyl transfer process was observed, which is in contrast with two recently reported studies that suggest nucleophilic assistance at tin to be important in the transmetalation step.An important side reaction in the coupling of poorly reactive vinyltriflates and most aryltriflates is the Pd-induced homocoupling of the stannane to form biaryls.The experimental factors that control this process were evaluated.

Catalyst tailoring for palladium-mediated cross coupling of arylstannanes with vinyl triflates

Vinyl triflates couple smoothly with a variety of arylstannanes provided a polar, aprotic solvent is used in conjunction with a "ligandless" palladium catalyst, or catalytic system involving weak ligands such as triphenylarsine. Commonly employed ligands, for example, triphenylphosphine, were found to strongly inhibit the coupling.