111474-74-9

Upstream product

• 1017609-37-8 YWI₉₂ 
• 91-56-5 indole-2,3-dione 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 3265-29-0 3-diazo-indolin-2-one 
• 100-66-3 methoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 59-48-3 2-oxoindole 
• 623-12-1 4-chloromethoxybenzene 
• 111500-91-5 3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one 

Downstream Products

• 1351707-85-1 C₂₅H₃₁N₃O₆ 
• 1463045-62-6 (±)-3-(4-methoxyphenyl)-3-(2-methylallyl)indolin-2-one 

Relevant academic research and scientific papers

Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives

Chiral N,N-4-(dimethylamino)pyridine (DMAP) derivatives, which can be readily prepared by the Ugi multicomponent reaction in a one-pot manner, have been efficiently applied to the enantioselective Steglich rearrangement of oxindole derivatives to give the

Electrochemical Umpolung C-H Functionalization of Oxindoles

Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.

The catalytic decarboxylative allylation of enol carbonates: The synthesis of enantioenriched 3-allyl-3′-aryl 2-oxindoles and the core structure of azonazine

The catalytic asymmetric synthesis of 3-allyl-3′-aryl 2-oxindoles has been shownviathe Pd(0)-catalyzed decarboxylative allylation of allylenol carbonates. This methodology provides access to a variety of 2-oxindole substrates (5a-v) with all-carbon quater

Synthesis of α-Aryl Oxindoles by Friedel-Crafts Alkylation of Arenes

α-Aryl oxindoles are accessed from isatin via a two-step procedure involving a phospha-Brook rearrangement and a Friedel-Crafts alkylation in a one-pot procedure. The use of 1,1,1,3,3,3-hexafluoro-2-propanol as solvent significantly extended the reaction

Organocatalytic stereoselective conjugate addition of 3-substituted oxindoles with in situ generated ortho-quinone methides

A novel method for the stereoselective conjugate addition of 3-substituted oxindoles to in situ generated o-QMs was described. This process was catalyzed efficiently by a cinchonidine-derived squaramide catalyst in oil-water phase, furnishing the corresponding 3,3-disubsituted oxindole derivatives in moderate to high yields (up to 98%) with high stereoselectivities (up to 95% ee, 15.4:1 dr). The utility of this reaction was also investigated by the gram-scale synthesis and derivatization of one of the products.

Asymmetric organocatalytic α-amination of 2-oxindoles with bis(2,2,2-trichloroethyl)azo-dicarboxylate

An enantioselective electrophilic amination of 3-substituted-2-oxindoles is reported, using bis(2,2,2-trichloroethyl)azo-dicarboxylate and commercially available Cinchona alkaloid organocatalysts. The best results were obtained in the reaction of 3-aryl s

Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me 2 -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd 2 (dba) 3 / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me 2 -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles

The asymmetric catalytic 1,6-addition of p-QMs with racemic oxindoles under the bifunctional catalysis of C2-symmetric dimeric Cinchona-derived squaramide is described. This tertiary amine-squaramide catalyzed reaction provides a diastereoselective and enantioselective approach to the effective assembly of diverse diarylmethine-substituted oxindoles having vicinal tertiary and quaternary stereocenters.

Sequential Au(i)/chiral tertiary amine catalysis: A tandem C-H functionalization of anisoles or a thiophene/asymmetric Michael addition sequence to quaternary oxindoles

We report an unprecedented sequential Au(i)/bifunctional tertiary amine catalysis, which enables a tandem C-H functionalization of weak nucleophiles (anisoles or thiophenes) and asymmetric Michael addition for the highly enantioselective synthesis of quaternary oxindoles from diazooxindoles and nitroenynes.

In situ generation of electrophilic trifluoromethylthio reagents for enantioselective trifluoromethylthiolation of oxindoles

An organocatalytic asymmetric trifluoromethylthiolation reaction via in situ generation of active electrophilic trifluoromethylthio species involving trichloroisocyanuric acid and AgSCF3 as a practical and easily handled electrophilic SCF3 source for CSP 3-SCF3 bond formation was developed. Reactions with this one-pot version strategy occurred in good yields and excellent stereoselectivities to access enantiopure oxindoles bearing a SCF 3-substituted quaternary chiral center. The straightforward process described here makes use of simple starting materials and proceeds under mild conditions, which will be useful in medicinal chemistry and diversity-oriented syntheses.