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 Downloads (Pure)

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
Journal	Organic and Biomolecular Chemistry
Early online date	08 Mar 2022
DOIs	https://doi.org/10.1039/d2ob00177b
Publication status	Early online date - 08 Mar 2022

Access to Document

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, 1.38 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
Dataset

File

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

File

Cite this

@article{251b012d703542bd96dcd233abe12999,

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.",

author = "Sweet, {Jamie S.} and Ruichen Wang and Panagiotis Manesiotis and Paul Dingwall and Knipe, {Peter C.}",

year = "2022",

month = mar,

day = "8",

doi = "10.1039/d2ob00177b",

language = "English",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - Atropselective Synthesis of N-Aryl Pyridones via Dynamic Kinetic Resolution Enabled by Non-Covalent Interactions

AU - Sweet, Jamie S.

AU - Wang, Ruichen

AU - Manesiotis, Panagiotis

AU - Dingwall, Paul

AU - Knipe, Peter C.

PY - 2022/3/8

Y1 - 2022/3/8

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.

U2 - 10.1039/d2ob00177b

DO - 10.1039/d2ob00177b

M3 - Article

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

ER -

Atropselective Synthesis of N-Aryl Pyridones via Dynamic Kinetic Resolution Enabled by Non-Covalent Interactions

Abstract

Access to Document

Fingerprint

Datasets

Dataset for "Atropselective synthesis of N-aryl pyridones via dynamic kinetic resolution enabled by noncovalent interactions"

Student Theses

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

Cite this