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- Title
Access to N‐Substituted 2‐Pyridones by Catalytic Intermolecular Dearomatization and 1,4‐Acyl Transfer.
- Authors
Xu, Guangyang; Chen, Ping; Liu, Pei; Tang, Shengbiao; Zhang, Xinhao; Sun, Jiangtao
- Abstract
A novel rhodium‐catalyzed dearomatization of O‐substituted pyridines to access N‐substituted 2‐pyridones has been developed. A computational study suggests a mechanism involving the formation of a pyridinium ylide followed by an unprecedented 1,4‐acyl migratory rearrangement from O to C. Furthermore, the chiral dirhodium complexes serve as the catalyst for the asymmetric transformation with excellent enantioselective control. DFT calculations indicate the chirality is transferred from axial chirality to the central stereogenic centre. The stronger π–π interaction and CH–π interaction account for the high enantioselectivity.
- Subjects
PYRIDONE; SUBSTITUENTS (Chemistry); DENSITY functional theory; INTERMOLECULAR forces; CATALYTIC activity; AROMATIZATION
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 7, p2002
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201812937