Iridium-Difluorphos-Catalyzed Asymmetric Hydrogenation of 2-Alkyl- and 2-Aryl-Substituted Quinoxalines: A General and Efficient Route into Tetrahydroquinoxalines

• Published in: Advanced synthesis & catalysis Vol. 352; no. 11-12; pp. 1886 - 1891
• Main Authors: Cartigny, Damien, Nagano, Takuto, Ayad, Tahar, Genêt, Jean-Pierre, Ohshima, Takashi, Mashima, Kazushi, Ratovelomanana-Vidal, Virginie
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 09.10.2010; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric catalysis; Asymmetry; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; difluorphos; Hydrogenation; iridium; Physical Sciences; quinoxaline; Quinoxalines; Science & Technology; Synthesis; tetrahydroquinoxalines; DESIGN; O-PHENYLENEDIAMINES; IMINES; COMPLEXES; asymmetric catalysis; hydrogenation; iridium; DIPHOSPHINE LIGAND; POTENT; tetrahydroquinoxalines; ENANTIOSELECTIVE HYDROGENATION; quinoxaline; INHIBITORS; ANTAGONISTS; DERIVATIVES; difluorphos
• ISSN: 1615-4150; 1615-4169; 1615-4169
• DOI: 10.1002/adsc.201000513

A highly efficient and general iridium‐difluorphos‐catalyzed asymmetric hydrogenation of diverse 2‐alkyl‐ and 2‐aryl‐substituted quinoxalines into biologically and pharmaceutically relevant 2‐substituted‐1,2,3,4‐tetrahydroquinoxaline units has been developed. High isolated yields and excellent enantioselectivities of up to 95% for 2‐alkyl‐substituted quinoxalines and of up to 94% for 2‐aryl‐substituted quinoxalines were obtained.