862907-25-3

Upstream product

• 139018-14-7 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one 
• 34619-03-9 tert-butyldicarbonate 
• 108-86-1 bromobenzene 
• 100-59-4 phenylmagnesium chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1402800-34-3 tert-butyl 3-hydroxy-2-oxo-3-phenylindoline-1-carboxylate 
• 160858-75-3 1-tert-butoxycarbonylisatin 
• 100-58-3 phenylmagnesium bromide 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 1289108-19-5 (R)-ethyl 2-(1,3-dioxoisoindolin-2-yl)-3-((S)-2-oxo-3-phenylindolin-3-yl)propanoate 
• 1289108-21-9 C₂₃H₂₄N₂O₅ 
• 1289108-23-1 (R)-2-acetamido-3-((S)-2-oxo-3-phenylindolin-3-yl)propanoic acid 
• 1289108-24-2 (R)-ethyl 2-acetamido-3-((S)-2-oxo-3-phenylindolin-3-yl)propanoate 
• 1289108-68-4 tert-butyl 3-(2-(1,3-dioxoisoindolin-2-yl)-3-ethoxy-3-oxopropyl)-2-oxo-3-phenylindoline-1-carboxylate 
• 1289108-15-1 tert-butyl 3-(2-(1,3-dioxoisoindolin-2-yl)-3-ethoxy-3-oxopropyl)-2-oxo-3-phenylindoline-1-carboxylate 
• 862907-00-4 (R)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate 
• 1040749-29-8 (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate 
• 1567850-19-4 (S)-tert-butyl 3-phenyl-3-(trifluoromethanesulfenyl)-2-oxoindoline-1-carboxylate 
• 1567850-21-8 (R)-tert-butyl 3-phenyl-3-(trifluoromethanesulfenyl)-2-oxoindoline-1-carboxylate 
• 1351708-13-8 (S)-3-amino-3-phenylindolin-2-one 
• 1453221-33-4 (R)-tert-butyl 3-(2-formylethyl)-2-oxo-3-phenylindoline-1-carboxylate 

Relevant academic research and scientific papers

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.

Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- A nd Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters

A copper-catalyzed asymmetric propargylic alkylation of propargylic acetates with 3-substituted oxindoles for the stereoselective construction of vicinal tertiary and all-carbon quaternary stereocenters in a 3,3-disubstituted oxindole skeleton has been realized. The reaction proceeded smoothly under the catalysis of Cu(MeCN)4PF6combined with a chiral tridentate ferrocenyl P,N,N ligand, leading to a broad range of optically active 3,3-disubstituted oxindoles in high yields and with excellent diastereo- A nd enantioselectivities.

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

Chincona alkaloid-catalyzed enantioselective trifluoromethylthiolation of oxindoles

An organocatalytic asymmetric trifluoromethylthiolation of 3-aryl or 3-alkyloxindoles employing a trifluoromethyl-substituted thioperoxide as the electrophilic trifluoromethylthiolating reagent was described. Reactions occurred in good to excellent enanti

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Iron(iii)-salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles

Chiral iron(iii)-salan complexes catalysed highly enantioselective α-fluorination and α-hydroxylation of β-keto esters and N-Boc oxindoles to give the corresponding products in high yields and good-to-excellent ee values under mild reaction conditions. This journal is the Partner Organisations 2014.

Facile synthesis of enantioenriched Cγ-tetrasubstituted α-amino acid derivatives via an asymmetric nucleophilic addition/protonation cascade

Chemical equations presented. An asymmetric nucleophilic addition/protonation reaction of 3-substituted oxindoles and ethyl 2-phthalimidoacrylate has been described. This strategy can give direct access to Cγ-tetrasubstituted α-amino acid derivatives bearing 1,3-nonadjacent stereocenters with up to 98% yield, 94:6 dr, and >99% ee. Dual activation is proposed in the transition state, and the opposite enantiomers can be obtained simply by changing cinchonidine-derived catalyst to the cinchonine analogue.

Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles

(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.

Catalytic enantioselective fluorination of oxindoles

We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluor