Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N-Aryl Quinolinium Salt

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Abstract

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. 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.

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Sweet, J. S., Rajkumar, S., Dingwall, P., & Knipe, P. C. (2021). Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N-Aryl Quinolinium Salt. European Journal of Organic Chemistry, 2021(29), 3980–3985. https://doi.org/10.1002/ejoc.202100188

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