Asymmetric Intramolecular Hydroamination to Construct Diverse N–N/C–N Indole Atropisomers via Cooperative Pd(0) and Chiral Phosphoric Acid Catalysis

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Here we present an enantioselective intramolecular hydroamination reaction of o-aminophenyl-1,3-enynes via cooperative catalysis Pd(0) and chiral phosphoric acid. This approach enables the efficient construction N–N/C–N axially stereogenic indoles with broad skeletal diversity high levels enantioselectivity in a completely atom-economic manner. Mechanistic studies indicate that protonation alkyne moiety π-Lewis base activation is favored, phosphate counteranion plays crucial role controlling atroposelectivity ring-closure step.

Language: Английский

Photoredox/nickel dual-catalyzed deaminative cross-electrophile for allenylic alkylation with non-activated alkyl katritzky salts

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5685 - 5694

Published: Jan. 1, 2024

The first allenylic alkylation with non-activated aliphatic amine derivatives, Katritzky salts, has been developed via photoredox/nickel dual-catalyzed reductive deaminative cross-electrophile coupling.

Language: Английский

Stereodivergent synthesis of chiral spiropyrazolones through Pd-catalyzed asymmetric sequential hydroalkylation of 1,3-enynes: unusual solvent effects on the enantioselectivity

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3033 - 3040

Published: Jan. 1, 2024

Chiral spiropyrazolones were constructed through Pd-catalyzed asymmetric sequential hydroalkylation of 1,3-enynes. Four stereoisomers could be obtained substrate control and chiral ligand control.

Language: Английский