Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Maximilian TiffnerMario Waser

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.

References

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Sep 15, 2017·Beilstein Journal of Organic Chemistry·Johannes SchörgenhumerMario Waser

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Citations

Feb 27, 2021·Chemical Reviews·Paramasivam SivaguruXihe Bi
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hideyasu ChinaToshifumi Dohi

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Methods Mentioned

BETA
NMR
column chromatography

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