Consecutive Asymmetric Transfer Hydrogenation of C2-Acylated Quinolines and Quinoxalines: A Diastereodivergent Synthesis of Enantioenriched Tetrahydroquinolines and Tetrahydroquinoxalines Bearing Endo- and Exocyclic Chirality

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: May 15, 2025

Consecutive asymmetric hydrogenation offers a direct and convenient approach to synthesizing complex C(sp3)-enriched products with multiple chirality. Herein, we report an synthesis of chiral 1,2,3,4-tetrahydroquinolines (THQs) tetrahydroquinoxalines bearing both endo- exocyclic vicinal chirality through the consecutive transfer easily accessible C2-acylated quinolines quinoxalines. The method features mild conditions, easy operation, broad substrate scope (42 examples), excellent control (generally >90% ee 20/1 dr). key success is use water-soluble aminobenzimidazole Ir catalyst. Mechanistic experiments support that reaction involves sequential reduction carbonyl group then quinoline core, each step dominated by Remarkably, diastereodivergent all four stereoisomers THQ has been successfully implemented.

Language: Английский

Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110081 - 110081

Published: June 1, 2024

Language: Английский