Method for synthesizing alpha, alpha-disubstituted dihydroquinoline by dearomatization of quinoline salt under catalysis of asymmetric rhodium
By adjusting the counterion of 2-substituted quinoline salt, and using an asymmetric rhodium catalytic system to perform nucleophilic addition reaction, the problem of asymmetric synthesis of chiral α, α-disubstituted dihydroquinoline in the prior art was solved, and efficient and excellent enantioselective synthesis was achieved.
Patent Information
- Application Number
- CN202311263856.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-09-27
- Publication Date
- 2025-03-28
AI Technical Summary
The prior art is difficult to efficiently synthesize chiral α,α-disubstituted dihydroquinolines with high efficiency, especially due to the presence of steric hindrance, such synthetic methods are challenging.
By appropriately adjusting the counterion of 2-substituted quinoline salt, an asymmetric rhodium catalytic system, including [Rh(COD)Cl]2 and chiral ligands, using organic bases and ethanol as solvents, asymmetric nucleophilic addition reactions are carried out to achieve dearomatic arylation and alkenylation of 2-substituted quinoline salt, and the chiral α,α-disubstituted dihydroquinoline is synthesized.
This method achieves high efficiency and excellent enantioselectivity (ee value can reach >99%), high yield (yield rate can reach 99%), easy operation, low energy consumption, and environmentally friendly, and is suitable for drug development and the preparation of natural products.