Angewandte Chemie International Edition
Volume 61, Issue 31 e202207944
Cover Picture
Free Access

Cover Picture: Sigmatropic [1,5] Carbon Shift of Transient C3 Ammonium Enolates (Angew. Chem. Int. Ed. 31/2022)

Garrit Wicker, 

Garrit Wicker

Department of Chemistry, Paderborn University, Warburger Strasse 100, 33098 Paderborn, Germany

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Rundong Zhou, 

Rundong Zhou

Department of Chemistry, Paderborn University, Warburger Strasse 100, 33098 Paderborn, Germany

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Dr. Roland Schoch, 

Dr. Roland Schoch

Department of Chemistry, Paderborn University, Warburger Strasse 100, 33098 Paderborn, Germany

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Prof. Dr. Jan Paradies, 

Corresponding Author

Prof. Dr. Jan Paradies

Department of Chemistry, Paderborn University, Warburger Strasse 100, 33098 Paderborn, Germany

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First published: 13 June 2022
https://doi.org/10.1002/anie.202207944

Graphical Abstract

The reaction path of the Lewis acid catalyzed intramolecular aza-Michael addition to form a C3 ammonium enolate is reported by Jan Paradies et al. in their Communication (e202204378). This transient intermediate rearranges diastereospecifically to the tetrahydroquinoline-4-one scaffold. The central structure in the picture represents the transition state of the diastereospecific sigmatropic [1,5] carbon shift which proceeds with retention of configuration on the migrating carbon center.

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The reaction path of the Lewis acid catalyzed intramolecular aza-Michael addition to form a C3 ammonium enolate is reported by Jan Paradies et al. in their Communication (e202204378). This transient intermediate rearranges diastereospecifically to the tetrahydroquinoline-4-one scaffold. The central structure in the picture represents the transition state of the diastereospecific sigmatropic [1,5] carbon shift which proceeds with retention of configuration on the migrating carbon center.

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