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

Published in Journal of the American Chemical Society. 2015, vol. 137, no. 36, p. 11582-11585
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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Research group Groupe Matile
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ZHAO, Yingjie et al. Asymmetric Anion-π Catalysis: Enamine Addition to Nitroolefins on π-Acidic Surfaces. In: Journal of the American Chemical Society, 2015, vol. 137, n° 36, p. 11582-11585. doi: 10.1021/jacs.5b07382 https://archive-ouverte.unige.ch/unige:75233

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Deposited on : 2015-09-16

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