Issue 12, 2022

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
27 Jan 2022
Accepted
08 Feb 2022
First published
08 Mar 2022
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2022,20, 2392-2396

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

J. S. Sweet, R. Wang, P. Manesiotis, P. Dingwall and P. C. Knipe, Org. Biomol. Chem., 2022, 20, 2392 DOI: 10.1039/D2OB00177B

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