940763-48-4

Upstream product

• 20780-74-9 7-bromoisatin 
• 620-05-3 iodomethylbenzene 
• 100-39-0 benzyl bromide 

Downstream Products

• 1263090-28-3 C₂₈H₂₀BrNO₄ 
• 1366042-98-9 1-benzyl-7-bromo-3-hydroxyindolin-2-one 
• 1366043-14-2 (R)-1-benzyl-7-bromo-3-hydroxy-3-((S)-2-nitro-1-phenylethyl)indolin-2-one 
• 1376615-75-6 C₂₉H₃₃BrN₂O₄ 
• 1391858-24-4 (2'S,3'R,4'S)-5',5'-diethyl 3',4'-dimethyl 1-benzyl-7-bromo-2-oxospiro[indoline-3,2'-pyrrolidine]-3',4',5',5'-tetracarboxylate 
• 1391858-37-9 (2'S,3'R)-5',5'-diethyl 3'-methyl 1-benzyl-7-bromo-2-oxospiro[indoline-3,2'-pyrrolidine]-3',5',5'-tricarboxylate 
• 1391860-27-7 (2'S,3'R,4'R)-5',5'-diethyl 3',4'-dimethyl 1-benzyl-7-bromo-2-oxospiro[indoline-3,2'-pyrrolidine]-3',4',5',5'-tetracarboxylate 
• 1391858-47-1 (2'R,3'S)-trimethyl 1-benzyl-7-bromo-2-oxo-3'-phenylspiro[indoline-3,2'-pyrrolidine]-3',5',5'-tricarboxylate 
• 1391858-31-3 (2'S,3'R,4'S)-tetramethyl 1-benzyl-7-bromo-2-oxospiro[indoline-3,2'-pyrrolidine]-3',4',5',5'-tetracarboxylate 
• 1391858-41-5 (2'S,3'R)-trimethyl 1-benzyl-7-bromo-2-oxospiro[indoline-3,2'-pyrrolidine]-3',5',5'-tricarboxylate 
• 1402818-24-9 C₁₈H₁₀BrN₃O 

Relevant academic research and scientific papers

Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles

An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.

Applications of Ytterbium(II) Reagent as Grignard Reagent and Single-Electron Transfer Reagent in the Synthesis of 3-Substituted 2-Oxindoles

The use of ytterbium(II) reagent as both nucleophilic reagent and single-electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent is reported. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for the preparation of 3-substituted 2-oxindoles was developed.

Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process

A highly enantioselective halogenation/semipinacol rearrangement of isatin-derived allylic alcohols has been developed with a chiral N,N′-dioxide/ScIII complex as catalyst. This strategy involved a pivotal stereodivergent kinetic resolution process and provided a facile and efficient entry to optically active halo-substituted quinolone derivatives and quinoline alkaloids with a quaternary stereocenter simultaneously under mild reaction conditions. Based on the control experiments together with kinetic studies and DFT calculations, a possible catalytic cycle was proposed to illustrate the reaction process and enantiocontrol.

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.

Asymmetric Conjugate Addition of Ethylene Sulfonyl Fluorides to 3-Amido-2-oxindoles: Synthesis of Chiral Spirocyclic Oxindole Sultams

An enantioselective conjugate addition of ethylene sulfonyl fluorides to 3-amido-2-oxindoles has been developed. Quinine-derived squaramides were identified as efficient catalysts. A series of spirocyclic oxindole sultams were prepared with excellent yields and enantioselectivities. A reaction mechanism via bifunctional activation was proposed.

Nickel(II)-Catalyzed Asymmetric Propargyl [2,3] Wittig Rearrangement of Oxindole Derivatives: A Chiral Amplification Effect

A highly enantioselective [2,3] Wittig rearrangement of oxindole derivatives was realized by using a chiral N,N′-dioxide/NiII complex as the catalyst under mild reaction conditions. A strong chiral amplification effect was observed, and allowed access to chiral 3-hydroxy 3-substituted oxindoles bearing allenyl groups in high yields and enantioselectivities (up to 92 % ee) by using a ligand with only 15 % ee. A reasonable explanation was given based on the experimental investigations and X-ray crystal structures of enantiomerically pure and racemic catalysts. Moreover, the first catalytic kinetic resolution of racemic oxindole derivatives by a [2,3] Wittig rearrangement was realized with high efficiency and stereoselectivity.

Asymmetric vinylogous Mukaiyama aldol reaction of isatins under bifunctional organocatalysis: Enantioselective synthesis of substituted 3-hydroxy-2-oxindoles

A highly enantioselective organocatalytic vinylogous Mukaiyama aldol reaction of silyloxy dienes and isatins under bifunctional organocatalysis is presented. Substituted 3-hydroxy-2-oxindoles are synthesised in good yields and enantioselectivities. These

Development of Novel Chloramphenicol Scaffold-Based Chiral Hydroxyl Oxazoline Ligands and Their Application to the Asymmetric Alkynylation of Isatins

The synthesis of new chloramphenicol base-derived chiral hydroxyl oxazoline ligands, and their use in the first Zn(OTf)2-catalyzed enantioselective alkynylation of isatins are described. This transformation features mild reaction conditions, a remarkably broad substrate scope, and excellent functional group tolerance, affording the corresponding tertiary propargylic alcohols in high yields and with high enantioselectivities. The application of chiral hydroxyl oxazolines as ligands in Zn(II)-catalyzed asymmetric alkynylation reactions is unprecedented. (Figure presented.).

Scaffold-inspired enantioselective synthesis of biologically important spiro[pyrrolidin-3,2'-oxindoles] with structural diversity through catalytic isatin-derived 1,3-dipolar cycloadditions

Catalytic asymmetric construction of the biologically important spiro[pyrrolidin-3,2'-oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98 % ee) has been established by using an organocat

Dioxindole in asymmetric catalytic synthesis: Direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes

The asymmetric Michael addition of dioxindoles to β-substituted nitroalkenes is reported. The bifunctional primary amine-thiourea A, by means of a non-covalent-based mode of catalysis, secures direct access to 3-substituted 3-hydroxyoxindole derivatives with high stereocontrol. The Royal Society of Chemistry 2012.