Journal
CHEMICAL SCIENCE
Volume 8, Issue 6, Pages 4299-4305Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc01042g
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Funding
- Imperial College London
- EPSRC [EP/L00352X/1]
- Royal Society
- EPSRC [EP/L00352X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/L00352X/1] Funding Source: researchfish
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We have identified an enantioselective copper-catalyzed O-to-N formal [1,3]-rearrangement to form N-propargylic-2-pyridones. This enantioconvergent O-to-N propargylic rearrangement occurs rapidly at ambient temperature and high enantioselectivity is observed for a range of 3-alkyl-substituted substrates. Stereochemical features include a mild kinetic enantioenrichment of the substrate and a non-linear relationship between product and ligand enantiopurity. Based on kinetic analyses and cross-over experiments, we put forward a mechanistic proposal involving Cu-acetylides as well as bimetallic intermediates in which coordination to the pyridyl nitrogen is likely a crucial binding interaction.
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