期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 7, 页码 1980-1984出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812937
关键词
asymmetric catalysis; carbenes; dearomatization; diazo compounds; rearrangement
资金
- NNSFC [21572024, 21572192]
- Shenzhen STIC [JCYJ20170412150343516]
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
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 pi-pi interaction and CH-pi interaction account for the high enantioselectivity.
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