50899-39-3

Upstream product

• 13057-17-5 bromethyl methyl ether 
• 107-30-2 chloromethyl methyl ether 
• 109-87-5 Dimethoxymethane 
• 91-56-5 indole-2,3-dione 
• 40899-68-1 1-(methoxymethyl)-1H-indole 
• 13057-19-7 Iodomethyl methyl ether 

Downstream Products

• 845512-60-9 3-hydroxy-1-methoxymethyl-3-phenyl-1,3-dihydro-indol-2-one 
• 845512-39-2 1-(methoxymethyl)-3-(phenyl)oxindole 
• 1227185-90-1 C₂₅H₃₀N₂O₈ 
• 1234379-46-4 C₂₃H₁₉N₃O₅ 
• 1374418-90-2 (2R,3R)-1'-(methoxymethyl)-3-phenyl-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione 
• 1443041-67-5 (2S,5S)-dibenzhydryl 1'-methoxymethyl-2'-oxo-5-vinyl-4,5-dihydro-3H-spiro[furan-2,3'-indoline]-3,3-dicarboxylate 
• 1618671-09-2 C₁₉H₁₄N₂O₃ 
• 1618671-21-8 C₃₁H₂₅N₃O₇ 

Relevant academic research and scientific papers

Chiral naphthyl-C2-indole as scaffold for phosphine organocatalysis: Application in asymmetric formal [4 + 2] cycloaddition reactions

The applications of a newly designed chiral naphthyl-C2-indole bifunctional phosphine organocatalyst in stereoselective formal [4 + 2] cycloaddition reactions were reported. The chiral naphthyl-C2-indole skeleton was introduced to bifunctional phosphine o

Organocatalytic and Late-Stage CH-Functionalization Enabled Asymmetric Synthesis of Communesin F and Putative Communesins

Herein we report the total syntheses of communesin F and putative members of the communesin family of polycyclic bis-aminal alkaloids. The successful strategy featured a novel organocatalytic reaction between two oxindole subunits to cast, after extensive optimization, the all-carbon vicinal quaternary stereocenters of the target molecule with high enantiocontrol. The resulting bis-oxindole intermediate further underwent a Ti(OiPr)4-mediated dehydrative skeletal rearrangement to furnish the communesin core structure. Consider the ready availability and low-cost of unsubstituted isatin, and the inferior organocatalytic reaction employing a bromo-substituted substrate, a Pd(OAc)2-catalyzed and oxalamide-directed aryl CH-alkenylation reaction was implemented to assemble the complete skeletal backbone of the target molecule. Collectively, the synthetic technologies disclosed herein constitute the first asymmetric organocatalytic approach to the communesins, together with a highly effective late-stage CH-functionalization in stark contrast to the bromoarene substrates employed in all of the past synthetic work.

Addition of carbamoylsilane to isatins: Highly efficient synthesis of 3-hydroxy-3-aminocarbonyl-2-oxindoles derivatives

The first addition reaction between isatins and carbamoysilane has been developed which provides 3-hydroxy-3-aminocarbonyl-2-oxindoles core structures with excellent yields. Moreover, the reaction could undergo a one-pot synthesis process to furnish 3-hydroxy-3-aminocarbonyl-2-oxindole with gram-scale.

Novel Methodology for the Efficient Synthesis of 3-Aryloxindoles: [1,2]-Phospha-Brook Rearrangement-Palladium-Catalyzed Cross-Coupling Sequence

A novel methodology for the efficient synthesis of 3-aryloxindoles from isatin derivatives was developed. The methodology involves the formation of an oxindole having a phosphate moiety at the C-3 position via the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis followed by palladium-catalyzed cross-coupling with aryl boron reagents. The one-pot synthesis of 3-aryloxindoles from isatin derivatives is also described.

Iodine-Catalyzed Oxidation of N-Substituted Indoles by using Chloramine-B: A Facile and Practical Approach to Isatins

An efficient method for the iodine-catalyzed oxidation of N-substituted indoles by using chloramine-B under mild reaction conditions was explored. This reaction was found to be tolerant to a variety of functional groups and provided the corresponding isatins in moderate to excellent yields. In addition, application of this method to the one-pot synthesis of 3-hydroxyoxindole and N-methylisatin oxime was realized.

Asymmetrie aldol reaction of acetaldehyde and isatin derivatives for the total syntheses of ent-convolutamydine e and cpc-1 and a half fragment of madindoline A and B

The asymmetric aldol reaction of isatin derivatives and acetaldehyde has been developed using 4-hydroxydiarylprolinol as a catalyst, affording the aldol products with high enantioselectivity, these products being key intermediates in the synthesis of 3-hy

Palladium-catalyzed asymmetric allylation of prochiral nucleophiles: Synthesis of 3-allyl-3-aryl oxindoles

Excellent yields and enantioselectivies are attained in the synthesis of 3-alkyl-3-aryl oxindoles based on the Pd-catalyzed asymmetric allylic alkylation (AAA) reaction. This approach utilizes a nonbasic hydroxylic additive in the transformation of 3-aryl

N-alkoxymethylation of secondary amides, sulfonamides and phosphamides using dialkoxymethanes in the presence of Lewis acids

A convenient and efficient one-pot synthesis of N-alkoxymethyl derivatives of secondary amides, sulfonamides and phosphamides in reaction with the appropriate dialkoxymethanes in the presence of a Lewis acid is described. In this method the use of toxic and carcinogenic chloromethyl alkyl ethers was eliminated.