Abstract
AbstractInspired by naturally occurring molecules containing atropisomeric N+‐C axes, we have developed a novel synthetic approach to generate a library of axially chiral N‐aryl quinolinium salts. Enantiopurities up to 93 % ee were obtained via a four‐step route from commercially available precursors. Axial stereochemistry was controlled through an enantioselective ring‐closing Buchwald–Hartwig coupling reaction. The structure and properties of the salts were examined by X‐ray crystallography, DFT, UV‐Vis, and fluorescence spectroscopy, revealing high rotational barriers and solvatochromic behaviour.
Highlights
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Inspired by naturally occurring molecules containing atropisomeric N + -C axes, we have developed a novel synthetic approach to generate a library of axially chiral N-aryl quinolinium salts
The synthesis of heterobiaryl atropisomers is less-developed than the all-carbon variants, though some effective strategies have been reported.[12,13,14,15,16]
Summary
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