Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions

Jamie S. Sweet; Ruichen Wang; Panagiotis Manesiotis; Paul Dingwall; Peter C. Knipe

doi:10.1039/d2ob00177b

Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions

Jamie S. Sweet, Ruichen Wang, Panagiotis Manesiotis, Paul Dingwall, Peter C. Knipe^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

5 Citations (Scopus)

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Abstract

The dynamic kinetic resolution of C–N atropisomeric pyridones was achieved via asymmetric phase-transfer catalysis, exploiting a rotational barrier-lowering hydrogen bond in the starting materials. X-ray and NMR experiments revealed the presence of a barrier-raising ground state CH⋯π interaction in the product, supported by DFT calculations. A co-crystal of the quinidine-derived phase-transfer catalyst and substrate reveals key substrate–catalyst non-covalent interactions.

Original language	English
Pages (from-to)	2392-2396
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	12
Early online date	08 Mar 2022
DOIs	https://doi.org/10.1039/d2ob00177b
Publication status	Published - 28 Mar 2022

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10.1039/d2ob00177bLicence: CC BY

Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions
Copyright 2022 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, 1.39 MBLicence: CC BY

Dataset for "Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by noncovalent interactions"
Dingwall, P. (Creator) & Knipe, P. (Owner), Queen's University Belfast, 2021
DOI: 10.17034/57c858bd-52ab-46c7-ac95-594e1fb66542
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Enantioselective synthesis of novel N-C atropisomers, their properties and potential applications
Sweet, J. (Author), Knipe, P. (Supervisor) & Dingwall, P. (Supervisor), Jul 2022
Student thesis: Doctoral Thesis › Doctor of Philosophy

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title = "Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions",

abstract = "The dynamic kinetic resolution of C–N atropisomeric pyridones was achieved via asymmetric phase-transfer catalysis, exploiting a rotational barrier-lowering hydrogen bond in the starting materials. X-ray and NMR experiments revealed the presence of a barrier-raising ground state CH⋯π interaction in the product, supported by DFT calculations. A co-crystal of the quinidine-derived phase-transfer catalyst and substrate reveals key substrate–catalyst non-covalent interactions.",

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AU - Sweet, Jamie S.

AU - Wang, Ruichen

AU - Manesiotis, Panagiotis

AU - Dingwall, Paul

AU - Knipe, Peter C.

PY - 2022/3/28

Y1 - 2022/3/28

N2 - The dynamic kinetic resolution of C–N atropisomeric pyridones was achieved via asymmetric phase-transfer catalysis, exploiting a rotational barrier-lowering hydrogen bond in the starting materials. X-ray and NMR experiments revealed the presence of a barrier-raising ground state CH⋯π interaction in the product, supported by DFT calculations. A co-crystal of the quinidine-derived phase-transfer catalyst and substrate reveals key substrate–catalyst non-covalent interactions.

AB - The dynamic kinetic resolution of C–N atropisomeric pyridones was achieved via asymmetric phase-transfer catalysis, exploiting a rotational barrier-lowering hydrogen bond in the starting materials. X-ray and NMR experiments revealed the presence of a barrier-raising ground state CH⋯π interaction in the product, supported by DFT calculations. A co-crystal of the quinidine-derived phase-transfer catalyst and substrate reveals key substrate–catalyst non-covalent interactions.

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DO - 10.1039/d2ob00177b

M3 - Article

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Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions

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Student theses

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

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