TY - JOUR
T1 - Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N‐Aryl Quinolinium Salt
AU - Sweet, Jamie Santiago
AU - Sundaram, Rajkumar
AU - Dingwall, Paul
AU - Knipe, Peter Clarke
PY - 2021/2/26
Y1 - 2021/2/26
N2 - 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‐Harwig 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.
AB - 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‐Harwig 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.
U2 - 10.1002/ejoc.202100188
DO - 10.1002/ejoc.202100188
M3 - Article
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
ER -