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DOI | 10.1126/science.aay2204 |
Light-driven deracemization enabled by excited-state electron transfer | |
Shin, Nick Y.1; Ryss, Jonathan M.2; Zhang, Xin1; Miller, Scott J.2; Knowles, Robert R.1 | |
2019-10-18 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 366期号:6463页码:364-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | Deracemization is an attractive strategy for asymmetric synthesis, but intrinsic energetic challenges have limited its development. Here, we report a deracemization method in which amine derivatives undergo spontaneous optical enrichment upon exposure to visible light in the presence of three distinct molecular catalysts. Initiated by an excited-state iridium chromophore, this reaction proceeds through a sequence of favorable electron, proton, and hydrogen-atom transfer steps that serve to break and reform a stereogenic C-H bond. The enantioselectivity in these reactions is jointly determined by two independent stereoselective steps that occur in sequence within the catalytic cycle, giving rise to a composite selectivity that is higher than that of either step individually. These reactions represent a distinct approach to creating out-of-equilibrium product distributions between substrate enantiomers using excited-state redox events. |
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:000491290000051 |
WOS关键词 | ARYL HALIDES ; STRATEGY ; THERMOCHEMISTRY ; ACTIVATION ; ALKENES |
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/202581 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Princeton Univ, Dept Chem, Princeton, NJ 08544 USA; 2.Yale Univ, Dept Chem, 225 Prospect St, New Haven, CT 06520 USA |
推荐引用方式 GB/T 7714 | Shin, Nick Y.,Ryss, Jonathan M.,Zhang, Xin,et al. Light-driven deracemization enabled by excited-state electron transfer[J]. SCIENCE,2019,366(6463):364-+. |
APA | Shin, Nick Y.,Ryss, Jonathan M.,Zhang, Xin,Miller, Scott J.,&Knowles, Robert R..(2019).Light-driven deracemization enabled by excited-state electron transfer.SCIENCE,366(6463),364-+. |
MLA | Shin, Nick Y.,et al."Light-driven deracemization enabled by excited-state electron transfer".SCIENCE 366.6463(2019):364-+. |
条目包含的文件 | 条目无相关文件。 |
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