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Heteroaromatic N-Oxides in Asymmetric Catalysis: A Review

Department of Organic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw, Poland
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Academic Editor: Zbigniew Czarnocki
Molecules 2020, 25(2), 330; https://doi.org/10.3390/molecules25020330 (registering DOI)
Received: 3 December 2019 / Revised: 10 January 2020 / Accepted: 12 January 2020 / Published: 14 January 2020
(This article belongs to the Special Issue Stereochemistry in Action)
An increasing interest in the synthesis and use of optically active pyridine N-oxides as chiral controllers for asymmetric reactions has been observed in the last few years. Chiral heteroaromatic N-oxides can work as powerful electron-pair donors, providing suitable electronic environments in the transition state formed within the reaction. The nucleophilicity of the oxygen atom in N-oxides, coupled with a high affinity of silicon to oxygen, represent ideal properties for the development of synthetic methodology based on nucleophilic activation of organosilicon reagents. The application of chiral N-oxides as efficient organocatalysts in allylation, propargylation, allenylation, and ring-opening of meso-epoxides, as well as chiral ligands for metal complexes catalyzing Michael addition or nitroaldol reaction, can also be found in the literature. This review deals with stereoselective applications of N-oxides, and how the differentiating properties are correlated with their structure. It contains more recent results, covering approximately the last ten years. All the reported examples have been divided into five classes, according to the chirality elements present in their basic molecular frameworks. View Full-Text
Keywords: chiral heteroaromatic N-oxides; organocatalysis; asymmetric transformations stereoselectivity chiral heteroaromatic N-oxides; organocatalysis; asymmetric transformations stereoselectivity
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Wrzeszcz, Z.; Siedlecka, R. Heteroaromatic N-Oxides in Asymmetric Catalysis: A Review. Molecules 2020, 25, 330.

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