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 |
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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 | |
Publication status | Published - 28 Mar 2022 |
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Dive into the research topics of 'Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions'. Together they form a unique fingerprint.Datasets
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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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Student theses
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Enantioselective synthesis of novel N-C atropisomers, their properties and potential applications
Author: Sweet, J., Jul 2022Supervisor: Knipe, P. (Supervisor) & Dingwall, P. (Supervisor)
Student thesis: Doctoral Thesis › Doctor of Philosophy
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