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DOI | 10.1126/science.aao5894 |
Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis | |
Banik, Steven M.; Levina, Anna; Hyde, Alan M.; Jacobsen, Eric N. | |
2017-11-10 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2017 |
卷号 | 358期号:6364页码:761-764 |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | Small-molecule dual hydrogen-bond (H-bond) donors such as ureas, thioureas, squaramides, and guanidinium ions enjoy widespread use as effective catalysts for promoting a variety of enantioselective reactions. However, these catalysts are only weakly acidic and therefore require highly reactive electrophilic substrates to be effective. We introduce here a mode of catalytic activity with chiral H-bond donors that enables enantioselective reactions of relatively unreactive electrophiles. Squaramides are shown to interact with silyl triflates by binding the triflate counterion to form a stable, yet highly Lewis acidic, complex. The silyl triflate-chiral squaramide combination promotes the generation of oxocarbenium intermediates from acetal substrates at low temperatures. Enantioselectivity in nucleophile additions to the cationic intermediates is then controlled through a network of noncovalent interactions between the squaramide catalyst and the oxocarbenium triflate. |
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:000414847100038 |
WOS关键词 | 4+3 CYCLOADDITION REACTIONS ; DIELS-ALDER REACTIONS ; EQUILIBRIUM ACIDITIES ; MUKAIYAMA ALDOL ; SQUARAMIDE ; ORGANOCATALYSIS ; CATIONS ; ALLENAMIDES ; FURAN ; DMSO |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
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/197281 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA |
推荐引用方式 GB/T 7714 | Banik, Steven M.,Levina, Anna,Hyde, Alan M.,et al. Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis[J]. SCIENCE,2017,358(6364):761-764. |
APA | Banik, Steven M.,Levina, Anna,Hyde, Alan M.,&Jacobsen, Eric N..(2017).Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis.SCIENCE,358(6364),761-764. |
MLA | Banik, Steven M.,et al."Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis".SCIENCE 358.6364(2017):761-764. |
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