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

Research output: Contribution to journalArticlepeer-review

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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 languageEnglish
JournalOrganic and Biomolecular Chemistry
Early online date08 Mar 2022
DOIs
Publication statusEarly online date - 08 Mar 2022

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