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DOI | 10.1126/science.aar8238 |
Interrupted carbonyl-olefin metathesis via oxygen atom transfer | |
Ludwig, Jacob R.1; Watson, Rebecca B.1; Nasrallah, Daniel J.1; Gianino, Joseph B.2; Zimmerman, Paul M.1; Wiscons, Ren A.1; Schindler, Corinna S.1 | |
2018-09-28 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 361期号:6409页码:1363-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | 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. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000446142200045 |
WOS关键词 | ENE REACTIONS ; MECHANISM |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/199689 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA; 2.BASF, Adv Mat & Syst Res, Wyandotte, MI USA |
推荐引用方式 GB/T 7714 | Ludwig, Jacob R.,Watson, Rebecca B.,Nasrallah, Daniel J.,et al. Interrupted carbonyl-olefin metathesis via oxygen atom transfer[J]. SCIENCE,2018,361(6409):1363-+. |
APA | Ludwig, Jacob R..,Watson, Rebecca B..,Nasrallah, Daniel J..,Gianino, Joseph B..,Zimmerman, Paul M..,...&Schindler, Corinna S..(2018).Interrupted carbonyl-olefin metathesis via oxygen atom transfer.SCIENCE,361(6409),1363-+. |
MLA | Ludwig, Jacob R.,et al."Interrupted carbonyl-olefin metathesis via oxygen atom transfer".SCIENCE 361.6409(2018):1363-+. |
条目包含的文件 | 条目无相关文件。 |
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