GSTDTAP  > 地球科学
DOI10.1126/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
ISSN0036-8075
EISSN1095-9203
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
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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-+.
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