1448544-18-0

Upstream product

• 122-00-9 para-methylacetophenone 
• 54779-81-6 4-methylacetophenone phenylhydrazone 
• 55577-25-8 2-(4-methylphenyl)-1H-indole 
• 595548-50-8 2-(4-methylphenyl)indoline 
• 552-89-6 2-nitro-benzaldehyde 

Relevant academic research and scientific papers

Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.

Enantioselective hydrogenation of N-heteroaromatics catalyzed by chiral diphosphine modified binaphthyl palladium nanoparticles

The first application of binaphthyl-stabilized palladium nanoparticles (Bin-PdNPs) with chiral modifiers in asymmetric hydrogenation of N-heteroaromatics is revealed. With an appropriate ratio of R-BINAP/Bin-PdNPs used, the pre-prepared chiral nanocatalyst achieves asymmetric hydrogenations of 2-substituted quinolines with good to excellent yields and moderate enantioselectivities, which showed superior catalytic properties to the R-BINAP/Pd complex. Moreover, this protocol is also applicable to 2-substituted indoles.

Kinetic resolution of indolines through reductive amination of aldehydes by chiral Br?nsted acid

We have developed a highly efficient and practical strategy for the kinetic resolution of indoline derivatives, involving a chiral Br?nsted acid-catalyzed iminium ion formation and asymmetric transfer hydrogenation cascade process. The kinetic resolution allows the synthesis of 2-substituted N-benzylindolines in good yields with moderate to excellent enantioselectivities.

Chiral phosphoric acid-catalyzed oxidative kinetic resolution of indolines based on transfer hydrogenation to imines

The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained in good yields with excellent enantioselectivities.