411237-64-4

Upstream product

• 1217-89-6 1-benzylisatin 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 91-56-5 indole-2,3-dione 
• 620-05-3 iodomethylbenzene 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 21728-28-9 (2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester 

Downstream Products

• 1327335-73-8 C₂₄H₂₅NO₅ 
• 1344679-30-6 (3R,4'R,5'R)-ethyl 1-benzyl-5'-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-2-oxo-2'-thioxospiro[indoline-3,3'-pyrrolidine]-4'-carboxylate 
• 1400564-39-7 C₂₅H₁₉NO₃ 
• 1429630-22-7 C₃₀H₂₈N₂O₅ 
• 13672-25-8 ethyl 2-(1-benzyl-2-oxoindolin-3-yl)acetate 

Relevant academic research and scientific papers

AlCl3-promoted selective michael addition with allenoate and methyleneindolinone: Synthesis of spirocyclic oxindole by using allenoate as a four-carbon component building block

The AlCl3-promoted cyclization of readily available allenoates with methyleneindolinone is disclosed. The present strategy provides a rapid access to spirocyclic oxindole-cyclohexenones in an efficient manner. Remarkably, the allenoate is implemented as a four-carbon (4C) component to form the ring, which shows high synthetic efficiency. Flexibility of this method allows quick synthesis of spirocyclic oxindole-dihydropyrans by varying one of the components. It is also noteworthy that AlCl3 serves as the chlorine source as well as an effective catalyst to facilitate this interesting transformation.

Enantioselectivity-switchable organocatalytic [4 + 2]-annulation to access the spirooxindole?norcamphor scaffold

An organocatalyzed enantiodivergent synthesis of a multifunctionalized spirooxindole?norcamphor scaffold via a [4 + 2]-annulation between cyclicα, β-unsaturated ketone and methylene indolinones has been established. The presence of CaCl2 in DMF could reverse the enantioselectivity to facilely deliver the enantiomers of the corresponding spirooxindoles. Both enantiomers of the corresponding spirooxindoles were obtained in excellent yield and diastereo-/enantioselectivity by employing one single prolinosulfonamide catalyst.

Metal-free visible-light-promoted intermolecular [2+2]-cycloaddition of 3-ylideneoxindoles

The Rose Bengal sensitized intermolecular [2?+?2]-cycloaddition of 3-ylideneoxindoles for the synthesis of spirocyclic oxindoles was developed successfully under visible light irradiation conditions. The cycloaddition products were obtained in good yields

Organocatalytic Aza-Michael/Michael Cyclization Cascade Reaction: Enantioselective Synthesis of Spiro-oxindole Piperidin-2-one Derivatives

A simple, direct, and highly enantioselective synthesis of spiro-oxindole piperidin-2-one derivatives was achieved through an aza-Michael/Michael cyclization cascade sequence using a squaramide catalyst. The desired products were obtained in excellent yields (up to 99%) and good to high stereoselectivities (up to >20:1 dr and up to 99% ee) under mild conditions.

Interrupted Morita-Baylis-Hillman-Type Reaction of α-Substituted Activated Olefins

It was demonstrated that 3-olefinic oxindoles could generate zwitterionic enolate species with tertiary phosphines and undergo C-C bond formation with various electrophiles in an interrupted Morita-Baylis-Hillman-type reaction manner, followed by a dephos

Generation of All-Carbon Quaternary Stereocenters at the C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement and Revision of Absolute Configuration: Total Synthesis of (-)-Physostigmine

A diastereoselective (up to >99%) route to all carbon quaternary stereocenters at the C-3 position of cyclic lactams has been developed via Johnson-Claisen rearrangement of ?-hydroxy-α,β-unsaturated lactams. It has been observed that olefin geometry plays an important role in the development of the absolute stereochemistry of the product. Dependence of product configuration on the olefin geometry is explained by postulating probable transition states. The success of this method has been shown for multigram-scale synthesis of these substituted lactams from commercially available cheap starting materials. The synthetic usefulness of this method is also demonstrated by carrying out the total synthesis of (a-)-physostigmine.

Base-catalyzed controllable reaction of 3-ylideneoxindoles with O-Boc hydroxycarbamates for the synthesis of amidoacrylates and spiroaziridine oxindoles

A base-catalyzed divergent reaction of 3-ylideneoxindoles with O-Boc hydroxycarbamates has been developed to provide efficient access to various amidoacrylates and spiroaziridine oxindoles with generally high yields, which should be potentially useful in drug discovery.

RETRACTED ARTICLE: An expeditious route to both enantiomers of all carbon quaternary stereocenters at C-3 carbon of lactams via [3,3]-sigmatropic rearrangement: Total synthesis of (-)-physostigmine

A diastereoselective route to all carbon quaternary stereocenters at the C-3 position of cyclic lactams has been developed via Johnson-Claisen rearrangement of γ-hydroxy-α, β-unsaturated lactams. It has been observed that olefin geometry plays an important role in the development of the absolute stereochemistry of the product. The dependence of the product configuration on the olefin geometry is explained by postulating probable transition states. The success of this method has been shown for the multigram scale synthesis of these substituted lactams from commercially available cheap starting materials. The synthetic usefulness of this method is also demonstrated by carrying out the total synthesis of (-)-physostigmine.

Synthesis of CF3-containing 3,3′-cyclopropyl spirooxindoles by sequential [3 + 2] cycloaddition/ring contraction of ylideneoxindoles with 2,2,2-trifluorodiazoethane

A [3 + 2] cycloaddition/ring contraction sequence of ylideneoxindoles with in situ-generated 2,2,2-trifluorodiazoethane without the use of any transition-metal catalyst has been developed. The reaction provides efficient access to biologically important a

Organocatalytic conjugate additions of acetylacetone to 3-ylideneoxindoles: A direct access to highly enantioenriched oxindole derivatives

A highly enantioselective organocatalytic conjugate addition of acetylacetone to 3-ylideneoxindoles is described. This method provides polysubstituted oxindoles in good to excellent enantioselectivities and high isolated yields. Georg Thieme Verlag Stuttg