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DOI | 10.1126/science.aaw4212 |
Hydrodealkenylative C(sp(3))-C(sp(2)) bond fragmentation | |
Smaligo, Andrew J.; Swain, Manisha; Quintana, Jason C.; Tan, Mikayla F.; Kim, Danielle A.; Kwon, Ohyun | |
2019-05-17 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 364期号:6441页码:681-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | Chemical synthesis typically relies on reactions that generate complexity through elaboration of simple starting materials. Less common are deconstructive strategies toward complexity-particularly those involving carbon-carbon bond scission. Here, we introduce one such transformation: the hydrodealkenylative cleavage of C(sp(3))-C(sp(2)) bonds, conducted below room temperature, using ozone, an iron salt, and a hydrogen atom donor. These reactions are performed in nonanhydrous solvents and open to the air; reach completion within 30 minutes; and deliver their products in high yields, even on decagram scales. We have used this broadly functionality tolerant transformation to produce desirable synthetic intermediates, many of which are optically active, from abundantly available terpenes and terpenoid-derived precursors. We have also applied it in the formal total syntheses of complex molecules. |
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:000468551000034 |
WOS关键词 | STEREOSELECTIVE-SYNTHESIS ; ENANTIOSPECIFIC SYNTHESIS ; TRANSFER HYDROGENATION ; REDOX REACTION ; DIELS-ALDER ; ACID ; KETONES ; ESTER ; REARRANGEMENT ; REDUCTION |
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/201439 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA |
推荐引用方式 GB/T 7714 | Smaligo, Andrew J.,Swain, Manisha,Quintana, Jason C.,et al. Hydrodealkenylative C(sp(3))-C(sp(2)) bond fragmentation[J]. SCIENCE,2019,364(6441):681-+. |
APA | Smaligo, Andrew J.,Swain, Manisha,Quintana, Jason C.,Tan, Mikayla F.,Kim, Danielle A.,&Kwon, Ohyun.(2019).Hydrodealkenylative C(sp(3))-C(sp(2)) bond fragmentation.SCIENCE,364(6441),681-+. |
MLA | Smaligo, Andrew J.,et al."Hydrodealkenylative C(sp(3))-C(sp(2)) bond fragmentation".SCIENCE 364.6441(2019):681-+. |
条目包含的文件 | 条目无相关文件。 |
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