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Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N ‐Aryl Quinolinium Salt
Author(s) -
Sweet Jamie S.,
Rajkumar Sundaram,
Dingwall Paul,
Knipe Peter C.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100188
Subject(s) - chemistry , atropisomer , solvatochromism , aryl , axial symmetry , molecule , enantioselective synthesis , salt (chemistry) , axial chirality , combinatorial chemistry , ring (chemistry) , stereochemistry , computational chemistry , crystallography , organic chemistry , catalysis , alkyl , structural engineering , engineering
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.