Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters
Maximilian Tiffner
Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040 Linz, Austria
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Academic Editors: Laura Palombi and Antonio Massa
Molecules 2018, 23(5), 1142; https://doi.org/10.3390/molecules23051142
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)
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.
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Keywords:
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
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MDPI and ACS Style
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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