期刊
SCIENCE
卷 361, 期 6409, 页码 1363-+出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aar8238
关键词
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资金
- NIH National Institute of General Medical Sciences [R01-GM118644]
- David and Lucile Packard Foundation
- Alfred P. Sloan Foundation
- National Science Foundation [CHE-1551994]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM118644] Funding Source: NIH RePORTER
Some of the simplest and most powerful carbon-carbon bond forming strategies take advantage of readily accessible ubiquitous motifs: carbonyls and olefins. Here we report a fundamentally distinct mode of reactivity between carbonyls and olefins that differs from established acid-catalyzed carbonyl-ene, Prins, and carbonyl-olefin metathesis reaction paths. A range of epsilon, zeta-unsaturated ketones undergo Bronsted acid-catalyzed intramolecular cyclization to provide tetrahydrofluorene products via the formation of two new carbon-carbon bonds. Theoretical calculations and accompanying mechanistic studies suggest that this carbocyclization reaction proceeds through the intermediacy of a transient oxetane formed by oxygen atom transfer. The complex polycyclic frameworks in this product class appear as common substructures in organic materials, bioactive natural products, and recently developed pharmaceuticals.
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