期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 130, 期 51, 页码 17266-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja807937m
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资金
- NIH [GM-079339]
- German Academic Exchange Service (DAAD)
Cyclic sulfonyl imines derived from ketones were identified as stable and readily prepared compounds that serve as superior electrophiles for N-heterocyclic carbene (NHC)-catalyzed annulations with a,p-unsaturated aldehydes to afford highly substituted y-lactams. Their superior reactivity and properties are highlighted by the first example of NHC-catalyzed reactions of enals with low catalyst loadings (0.5 mol %) and broad substrate scope encompassing alkyl, aryl, and heteroaromatic substituents. These findings and supporting studies suggest an alternative, ene-like mechanism rather than the catalytic generation of a catalyst-bound homoenolate equivalent.
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