Journal
ORGANIC LETTERS
Volume 20, Issue 1, Pages 64-67Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03358
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Funding
- NSFC [21502192, 21402199]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- Chinese Recruitment Program of Global Experts
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The umpolung of beta,gamma-unsaturated diketones through N-heterocyclic carbene catalysis is described, which allows access to a variety of highly functionalized bicyclic cydohexene-beta-lactones and 1,3,4-triaryl benzenes. An unprecedented reaction pattern involving the catalytic formation of nucleophilic O-acylated homoenolate intermediate is proposed. A diverse set of transformations on the product further showed the synthetic potential of this protocol.
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