926031-24-5

Upstream product

• 591-87-7 Allyl acetate 
• 3335-97-5 1-methyl-3-phenylindolin-2-one 
• 1222096-74-3 N-(2-bromophenyl)-N-methyl-2-phenyl-pent-4-enamide 
• 70122-89-3 tert-butyl allyl carbonate 
• 175467-46-6 2-diazo-N-methyl-N,2-diphenylacetamide 
• 211116-79-9 C₁₇H₁₅NO₂ 
• 4519-28-2 tetramethylphosphonium bromide 
• 862906-97-6 tert-butyl 2-oxo-3-phenylindoline-1-carboxylate 
• 100-61-8 N-methylaniline 
• 40669-47-4 N-methyl-N,2-diphenylacetamide 
• 1319774-50-9 allyl 3-(methyl(phenyl)amino)-3-oxo-2-phenylpropanoate 
• 103-82-2 phenylacetic acid 
• 153704-11-1 N-(2-bromophenyl)-N-methylacetamide 
• 108-90-7 chlorobenzene 

Downstream Products

• 211116-79-9 C₁₇H₁₅NO₂ 

Relevant academic research and scientific papers

Combining Ru-Catalyzed C-H Functionalization with Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of 3-Allyl-3-aryl Oxindole Derivatives from Aryl α-Diazoamides

Ruthenium-catalyzed C-H functionalization was successfully combined with palladium-catalyzed asymmetric allylic alkylation in one pot. The novel dual-metal-catalyzed reaction provides a variety of 3-allyl-3-aryl oxindoles from the corresponding α-diazoamides in up to 99% yield with up to 85% ee. The appropriate ligand choice is important to promote the sequential reaction, avoiding undesired metal interaction or ligand exchange.

Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles

The first phosphine-catalyzed enantioselective γ-addition with prochiral nucleophiles and 2,3-butadienoates as the reaction partners has been developed. Both 3-alkyl- and 3-aryl-substituted oxindoles could be employed in this process, which is catalyzed by a chiral phosphine that is derived from an amino acid, thus affording oxindoles that bear an all-carbon quaternary center at the 3-position in high yields and excellent enantioselectivity. The synthetic value of these γ-addition products was demonstrated by the formal total synthesis of two natural products and by the preparation of biologically relevant molecules and structural scaffolds.

Asymmetric decarboxylative allylation of oxindoles

An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excell

Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: Reaction development and applications

We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.

Highly chemo- and enantioselective synthesis of 3-Allyl-3-aryl oxindoles via the direct palladium-catalyzed α-arylation of amides

Figure presented A new NHC·Pd-catalyzed asymmetric α-arylation of amides is reported that gives direct access to synthetically valuable, allylated oxindoles with quaternary carbon centers. The reaction is made possible by the introduction of a new chiral NHC ligand. The palladium complexes derived therefrom combine excellent reactivity with high chemo- and enantioselectivity for the title transformation.

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