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Molecules 2018, 23(5), 1142; https://doi.org/10.3390/molecules23051142

Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters

Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria
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Academic Editors: Laura Palombi and Antonio Massa
Received: 20 April 2018 / Revised: 4 May 2018 / Accepted: 10 May 2018 / Published: 11 May 2018
(This article belongs to the Special Issue Enantioselective Catalysis)
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Abstract

Detailed investigations concerning the organocatalytic (asymmetric) α-azidation of prochiral β-ketoesters were carried out. It was shown that the racemic version of such a reaction can either be carried out under oxidative conditions using TMSN3 as the azide-source with quaternary ammonium iodides as the catalysts, or by using hypervalent iodine-based electrophilic azide-transfer reagents with different organocatalysts. In addition, the latter strategy could also be carried out with modest enantioselectivities when using simple cinchona alkaloid catalysts, albeit with relatively low yields. View Full-Text
Keywords: azides; organocatalysis; hypervalent iodine reagents; ammonium iodides; cinchona alkaloids azides; organocatalysis; hypervalent iodine reagents; ammonium iodides; cinchona alkaloids
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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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Tiffner, M.; Stockhammer, L.; Schörgenhumer, J.; Röser, K.; Waser, M. Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters. Molecules 2018, 23, 1142.

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