Abstract
Eight pyridine-containing and four 1,2,4-triazine-containing chiral oxazoline ligands incorporating electron-withdrawing substituents have been synthesized by two-step route including Buchwald–Hartwig amination. Enantio-inducing activity of the ligands has been assessed in the copper-catalyzed asymmetric nitroaldol reactions and the influence of the electron-withdrawing substituents on the ligands' activity has been investigated.Graphical abstract
Highlights
Metal-based asymmetric catalysis has proven to be a useful tool for preparation of enantiomerically pure compounds [1, 2]
According to our ongoing research project focusing on the synthesis and application of ligands that combine in their structures chiral oxazoline and six-membered aza-heteroaromatic rings, we have examined ligands with 1,2,4-triazine 1a-1d
3-bromo-5-phenyl-1,2,4-triazine (10) was subjected to C–N palladium-coupling with 2-(o-aminophenyl)oxazolines 8c-8f yielding 1,2,4-triazine ligands 5a-5d (Scheme 3)
Summary
Metal-based asymmetric catalysis has proven to be a useful tool for preparation of enantiomerically pure compounds [1, 2].
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