Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 50, Pages 13780-13784Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407935
Keywords
allenes; asymmetric allylation; reaction mechanisms; 2-pyridones; rhodium
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Funding
- DFG
- International Research Training Group Catalysts and Catalytic Reactions for Organic Synthesis [IRTG 1038]
- Krupp Foundation
- Alexander von Humboldt Foundation
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A rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes to give branched N-allyl 2-pyridones is reported. Preliminary mechanistic studies support the hypothesis that the reaction was initiated from the more acidic 2-hydroxypyridine form, and the initial kinetic O-allylation product was finally converted into the thermodynamically more stable N-allyl 2-pyridones.
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