期刊
NATURE CHEMISTRY
卷 6, 期 5, 页码 448-452出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.1917
关键词
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资金
- National Science Foundation (NSF) [CHE1265956]
- National Institutes of Health [CA031841]
- NSF Graduate Research Fellowship
- Abbott Laboratories Stanford Graduate Fellowship
- Kanazawa University
- German Academic Exchange Service
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1265956] Funding Source: National Science Foundation
- Grants-in-Aid for Scientific Research [26460004] Funding Source: KAKEN
Multicomponent reactions allow for more bond-forming events per synthetic operation, enabling more step-and time-economical conversion of simple starting materials to complex and thus value-added targets. These processes invariably require that reactivity be relayed from intermediate to intermediate over several mechanistic steps until a termination event produces the final product. Here, we report a multicomponent process in which a novel 1,2,3-butatriene equivalent (TMSBO: TMSCH2C CCH2OH) engages chemospecifically as a two-carbon alkyne component in a metal-catalysed [5+2] cycloaddition with a vinylcyclopropane to produce an intermediate cycloadduct. Under the reaction conditions, this intermediate undergoes a remarkably rapid 1,4-Peterson elimination, producing a reactive four-carbon diene intermediate that is readily intercepted in either a metal-catalysed or thermal [4+2] cycloaddition. TMSBO thus serves as an yne-to-diene transmissive reagent coupling two powerful and convergent cycloadditions-the homologous Diels-Alder and Diels-Alder cycloadditions-through a vinylogous Peterson elimination, and enabling flexible access to diverse polycycles.
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