Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 9, Pages 3135-3139Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510106
Keywords
1,4-addition; 2-aryl propionates; enantioselective catalysis; N-heterocyclic carbenes; -azolium ylides
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Funding
- Australian Research Council [DP120101315]
- Future Fellowship [FT110100319]
- Australian Research Council [FT110100319] Funding Source: Australian Research Council
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N-Heterocyclic carbene-catalyzed formation of -anionic intermediates from enones has been employed in the enantioselective synthesis of 2-aryl propionates. The reaction was achievable using a homochiral 4-MeOC6H4 morpholinone catalyst allowing the first example of enantioselective catalysis by umpolung of ,-unsaturated ketones. The reaction is high yielding, and shows robustness with reasonable generality. A mechanism is proposed in which the enantiodetermining protonation is achieved using either hexafluoroisopropanol or the formed naphthol product.
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