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

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JournalJournal of the American Chemical Society
DateE-pub ahead of print - 8 Sep 2015
DatePublished (current) - 16 Sep 2015
Issue number36
Volume137
Number of pages4
Pages (from-to)11582-11585
Early online date8/09/15
Original languageEnglish

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.

    Research areas

  • Alkenes/chemistry, Amines/chemistry, Anions, Catalysis, Hydrogen-Ion Concentration, Nitro Compounds/chemistry, Stereoisomerism, Surface Properties

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