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

Jamie S. Sweet; Sundaram Rajkumar; Paul Dingwall; Peter C. Knipe

doi:10.1002/ejoc.202100188

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

Jamie S. Sweet, Sundaram Rajkumar, Paul Dingwall, Peter C. Knipe

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

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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‐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.

Original language	English
Pages (from-to)	3980-3985
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2021
Issue number	29
Early online date	26 Feb 2021
DOIs	https://doi.org/10.1002/ejoc.202100188
Publication status	Published - 04 Aug 2021

Keywords

Organic Chemistry
Physical and Theoretical Chemistry

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10.1002/ejoc.202100188Licence: CC BY

Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N-Aryl Quinolinium Salt
Copyright 2021 the authors. This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 2.93 MBLicence: CC BY

Enantioselective synthesis of novel N-C atropisomers, their properties and potential applications
Author: Sweet, J., Jul 2022
Supervisor: Knipe, P. (Supervisor) & Dingwall, P. (Supervisor)
Student thesis: Doctoral Thesis › Doctor of Philosophy

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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‐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.",

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T1 - Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N‐Aryl Quinolinium Salt

AU - Sweet, Jamie S.

AU - Rajkumar, Sundaram

AU - Dingwall, Paul

AU - Knipe, Peter C.

PY - 2021/8/4

Y1 - 2021/8/4

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.

KW - Organic Chemistry

KW - Physical and Theoretical Chemistry

U2 - 10.1002/ejoc.202100188

DO - 10.1002/ejoc.202100188

M3 - Article

VL - 2021

SP - 3980

EP - 3985

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 29

ER -

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

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Enantioselective synthesis of novel N-C atropisomers, their properties and potential applications

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