期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 12, 页码 6425-6429出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202016771
关键词
asymmetric catalysis; heterogeneous catalysis; hydrogenation; lactams; nitrogen heterocycles
资金
- European Research Council (ERC) [788558]
- Deutsche Forschungsgemeinschaft (Leibniz Award)
- Alfried Krupp von Bohlen und Halbach Foundation
- Projekt DEAL
- European Research Council (ERC) [788558] Funding Source: European Research Council (ERC)
This study successfully demonstrates the synthesis of sought-after, enantioenriched delta-lactams through an interrupted hydrogenation mechanism using oxazolidinone-substituted pyridines and water.
Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chemical complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work we report the synthesis of sought-after, enantioenriched delta-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.
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