Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 17, Pages 5658-5661Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b02219
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Funding
- Singapore's National Research Foundation (NRF)
- Ministry of Education (MOE)
- Nanyang Technological University (NTU)
- China's National Key Program for Basic Research [2010CB 126105]
- Thousand Talent Plan, National Natural Science Foundation [21132003, 21472028]
- Guizhou Province Returned Oversea Student Science and Technology Activity Program
- Guizhou University
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An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a delta-LUMO activation of alpha,beta-gamma,delta-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote delta-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.
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