A highly cis-selective and enantioselective metal-free hydrogenation of 2,3-disubstituted quinoxalines.
A wide range of 2,3-disubstituted quinoxalines have been successfully hydrogenated with H2 using borane catalysts to produce the desired tetrahydroquinoxalines in 80-99% yields with excellent cis selectivity. Significantly, the asymmetric reaction employing chiral borane catalysts generated by the in situ hydroboration of chiral dienes with HB(C6F5)2 under mild reaction conditions has also been achieved with up to 96% ee, and represents the first catalytic asymmetric system to furnish optically active cis-2,3-disubstituted 1,2,3,4-tetrahydroquinoxalines.
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China).
Zhenhua
Z
Zhang
Haifeng
H
Du
D006859:Hydrogen / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D011810:Quinoxalines / Q000737:chemistry*; D013237:Stereoisomerism
D008670:Metals; D011810:Quinoxalines; D006859:Hydrogen
asymmetric catalysis; boron; diastereoselectivity; heterocycles; hydrogenation