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Catalysts 2019, 9(4), 327; https://doi.org/10.3390/catal9040327

Synthesis and Organocatalytic Asymmetric Nitro-aldol Initiated Cascade Reactions of 2-Acylbenzonitriles Leading to 3,3-Disubstituted Isoindolinones

1
Dipartimento di Chimica e Biologia, Università di Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, SA, Italy
2
Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria
*
Authors to whom correspondence should be addressed.
Received: 7 March 2019 / Revised: 27 March 2019 / Accepted: 28 March 2019 / Published: 2 April 2019
(This article belongs to the Special Issue Catalysts for Henry Reaction)
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Abstract

In this work, we investigated two strategies for the synthesis of the challenging ketones 2-acylbenzonitriles and we report their use as electrophiles in asymmetric organocatalytic cascade reactions with nitromethane. Promising results were obtained in the presence of chiral bifunctional ammonium salts under phase transfer conditions, which led to novel 3,3-disubstituted isoindolinones in quantitative yields and moderate enantioselectivity. View Full-Text
Keywords: cascade reactions; Henry-reactions; asymmetric organocatalysis; isoindolinone; heterocycles; ketones as electrophiles cascade reactions; Henry-reactions; asymmetric organocatalysis; isoindolinone; heterocycles; ketones as electrophiles
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Romano, F.; Di Mola, A.; Palombi, L.; Tiffner, M.; Waser, M.; Massa, A. Synthesis and Organocatalytic Asymmetric Nitro-aldol Initiated Cascade Reactions of 2-Acylbenzonitriles Leading to 3,3-Disubstituted Isoindolinones. Catalysts 2019, 9, 327.

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