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