Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 28, Pages 9984-9987Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501632
Keywords
antimicrobial activity; gamma-carbon addition; enals; N-heterocyclic carbenes; organocatalysis; reaction mechanisms
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Funding
- Singapore National Research Foundation
- Ministry of Education
- Nanyang Technological University (NTU)
- China's National Key program for Basic Research [2010CB 126105]
- Thousand Talent Plan
- National Natural Science Foundation of China [21132003, 21472028]
- Returned Oversea Student Science and Technology Activity Program of Guizhou Province
- Guizhou University
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The reaction mechanism of the -carbon addition of enal to imine under oxidative N-heterocyclic carbene catalysis is studied experimentally. The oxidation, -carbon deprotonation, and nucleophilic addition of -carbon to imine were found to be facile steps. The results of our study also provide highly enantioselective access to tricyclic sulfonyl amides that exhibit interesting antimicrobial activities against X. oryzae, a bacterium that causes bacterial disease in rice growing.
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