Asymmetric Anion-π Catalysis: Enamine Addition to Nitroolefins on π-Acidic Surfaces

Journal of the American Chemical Society
Yingjie ZhaoStefan Matile

Abstract

Here we provide experimental evidence for anion-π catalysis of enamine chemistry and for asymmetric anion-π catalysis. A proline for enamine formation on one side and a glutamic acid for nitronate protonation on the other side are placed to make the enamine addition to nitroolefins occur on the aromatic surface of π-acidic naphthalenediimides. With increasing π acidity of the formally trifunctional catalysts, rate and enantioselectivity of the reaction increase. Mismatched and more flexible controls reveal that the importance of rigidified, precisely sculpted architectures increases with increasing π acidity as well. The absolute configuration of stereogenic sulfoxide acceptors at the edge of the π-acidic surface has a profound influence on asymmetric anion-π catalysis and, if perfectly matched, affords the highest enantio- and diastereoselectivity.

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Citations

Mar 16, 2016·Journal of the American Chemical Society·Yingjie ZhaoStefan Matile
Jul 15, 2016·ACS Central Science·Yoann CotelleStefan Matile
Jul 20, 2016·Journal of the American Chemical Society·Sebastian BenzStefan Matile
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Dec 15, 2015·Chemistry : a European Journal·François N MirosStefan Matile
Aug 2, 2017·Chemistry : a European Journal·Martin NovákCina Foroutan-Nejad
Aug 20, 2020·Physical Chemistry Chemical Physics : PCCP·Glaucio R NagurniakGiovanni F Caramori
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Dec 19, 2018·Journal of the American Chemical Society·De-Hui TuoDe-Xian Wang
Oct 19, 2021·Chemistry : a European Journal·Na LuoQi-Qiang Wang

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